[ CAS No. 108166-01-4 ]

Name: 108166-01-4|Methyl 2-methylquinoline-6-carboxylate|98%
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SKU: A458157
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Quality Control of [ 108166-01-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 108166-01-4 ]

SDS

Alternatived Products of [ 108166-01-4 ]

Product Details of [ 108166-01-4 ]

CAS No. :	108166-01-4	MDL No. :	MFCD02690144
Formula :	C₁₂H₁₁NO₂	Boiling Point :	320.3±22.0°C at 760 mmHg
Linear Structure Formula :	-	InChI Key :	-
M.W :	201.22 g/mol	Pubchem ID :	2308822
Synonyms :

Calculated chemistry of of [ 108166-01-4 ]

Physicochemical Properties

Num. heavy atoms :	15
Num. arom. heavy atoms :	10
Fraction Csp3 :	0.17
Num. rotatable bonds :	2
Num. H-bond acceptors :	3.0
Num. H-bond donors :	0.0
Molar Refractivity :	57.99
TPSA :	39.19 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.8 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.42
Log Po/w (XLOGP3) :	2.44
Log Po/w (WLOGP) :	2.33
Log Po/w (MLOGP) :	1.91
Log Po/w (SILICOS-IT) :	2.78
Consensus Log Po/w :	2.38

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.99
Solubility :	0.208 mg/ml ; 0.00103 mol/l
Class :	Soluble
Log S (Ali) :	-2.91
Solubility :	0.25 mg/ml ; 0.00124 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.17
Solubility :	0.0136 mg/ml ; 0.0000678 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.41

Safety of [ 108166-01-4 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 108166-01-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 108166-01-4 ]
Downstream synthetic route of [ 108166-01-4 ]

[ 108166-01-4 ] Synthesis Path-Upstream 1~6

1
[ 67-56-1 ]
[ 635-80-3 ]
[ 108166-01-4 ]

Yield	Reaction Conditions	Operation in experiment
59%	at 0 - 65℃; for 12 h;	Step 2: methyl 2-methylquinoline-6-carboxylate: To a solution of 2-methylquinoline-6- carboxylic acid (3.0 g, 16.20 mmol) in methanol (30 ml.), sulphuric acid ( 3ml) was added dropwise at 0°C and then stirred at 65°C for 12h. The reaction mixture was concentrated and to the residue dichloromethane and aqueous sodium carbonate solutions were added. The organic layer was dried with sodium sulphate and concentrated to afford the title compound as a brown solid (1.9 g, 59percent).
59%	at 0 - 65℃; for 12 h;	Step 2: methyl 2-methylquinoline-6-carboxylate To a solution of 2-methylquinoline-6-carboxylic acid (3.0 g, 16.20 mmol) in methanol (30 ml.), sulphuric acid (3 ml) was added dropwise at 0° C. and then stirred at 65° C. for 12 h. The reaction mixture was concentrated and to the residue dichloromethane and aqueous sodium carbonate solutions were added. The organic layer was dried with sodium sulphate and concentrated to afford the title compound as a brown solid (1.9 g, 59percent).

Reference： [1] Journal of Heterocyclic Chemistry, 1989, vol. 26, p. 929 - 931
[2] Angewandte Chemie - International Edition, 2016, vol. 55, # 40, p. 12224 - 12227[3] Angew. Chem., 2016, vol. 128, # 40, p. 12412 - 12415,4
[4] Patent: WO2013/144737, 2013, A2, . Location in patent: Paragraph 252
[5] Patent: US2015/57309, 2015, A1, . Location in patent: Paragraph 0525
[6] Patent: WO2015/49535, 2015, A1, . Location in patent: Paragraph 00321

2
[ 598-32-3 ]
[ 17012-22-5 ]
[ 108166-01-4 ]

Reference： [1] Organic Letters, 2017, vol. 19, # 10, p. 2494 - 2497

3
[ 109-92-2 ]
[ 619-45-4 ]
[ 108166-01-4 ]

Reference： [1] Angewandte Chemie - International Edition, 2011, vol. 50, # 33, p. 7670 - 7673

4
[ 19718-49-1 ]
[ 108166-01-4 ]

Reference： [1] Organic and Biomolecular Chemistry, 2017, vol. 15, # 30, p. 6349 - 6352

5
[ 150-13-0 ]
[ 108166-01-4 ]

Reference： [1] Patent: WO2013/144737, 2013, A2,
[2] Patent: US2015/57309, 2015, A1,

6
[ 635-80-3 ]
[ 108166-01-4 ]

Reference： [1] J. Gen. Chem. USSR (Engl. Transl.), 1987, vol. 57, p. 96 - 99[2] Zhurnal Obshchei Khimii, 1987, vol. 57, # 1, p. 113 - 117

[ 108166-01-4 ] Synthesis Path-Downstream 1~4

1
[ 67-56-1 ]
[ 635-80-3 ]
[ 108166-01-4 ]

Yield	Reaction Conditions	Operation in experiment
59%	With sulfuric acid; at 0 - 65℃; for 12h;	Step 2: methyl 2-methylquinoline-6-carboxylate: To a solution of 2-methylquinoline-6- carboxylic acid (3.0 g, 16.20 mmol) in methanol (30 ml.), sulphuric acid ( 3ml) was added dropwise at 0C and then stirred at 65C for 12h. The reaction mixture was concentrated and to the residue dichloromethane and aqueous sodium carbonate solutions were added. The organic layer was dried with sodium sulphate and concentrated to afford the title compound as a brown solid (1.9 g, 59%).
59%	With sulfuric acid; at 0 - 65℃; for 12h;	Step 2: methyl 2-methylquinoline-6-carboxylate To a solution of <strong>[635-80-3]2-methylquinoline-6-carboxylic acid</strong> (3.0 g, 16.20 mmol) in methanol (30 ml.), sulphuric acid (3 ml) was added dropwise at 0 C. and then stirred at 65 C. for 12 h. The reaction mixture was concentrated and to the residue dichloromethane and aqueous sodium carbonate solutions were added. The organic layer was dried with sodium sulphate and concentrated to afford the title compound as a brown solid (1.9 g, 59%).
	With hydrogenchloride; In 1,4-dioxane; at 20 - 80℃; for 7h;Inert atmosphere;	[00321] To a solution of <strong>[635-80-3]2-methylquinoline-6-carboxylic acid</strong> (1 .5 g, 8.01 mmol) in dry methanol (18 mL) under argon at room temperature, HCI in dioxane (8.01 ml_, 32.1 mmol) was added dropwise and the resulting mixture was heated at 85C for 7 hours. Then it was cooled, concentrated, diluted with ethyl acetate and washed with NaOH 1 N (2 x 20 mL), water (1 x 20 mL) and brine (1 x 20 mL). Dried over Na2S04, filtered and concentrated under vacuum to afford the crude product methyl-2-methylquinoline-6- carboxylate as a pink solid (1 .44 g, 89%) which was carried onto the next step without purification. To a suspension of selenium dioxide (0.873 g, 7.87 mmol) in dry dioxane (1 1 mL) under argon at room temperature methyl-2-methylquinoline-6-carboxylate (1 .44 g, 7.16 mmol) was added in one portion and the resulting suspension was allowed to stir at 80 C for 18 hours. The reaction was allowed to cool to room temperature, filtered through Celite and concentrated under vacuum to afford an orange solid as crude product which was purified via flash column chromatography on silica gel in gradient from 10 to 20% ethyl acetate in petroleum ether to afford the clean product as a pale yellow solid (1 .28 g, 83%).

Reference： [1]Journal of Heterocyclic Chemistry,1989,vol. 26,p. 929 - 931
[2]Angewandte Chemie - International Edition,2016,vol. 55,p. 12224 - 12227
Angew. Chem.,2016,vol. 128,p. 12412 - 12415,4
[3]Patent: WO2013/144737,2013,A2 .Location in patent: Paragraph 252
[4]Patent: US2015/57309,2015,A1 .Location in patent: Paragraph 0525
[5]Patent: WO2015/49535,2015,A1 .Location in patent: Paragraph 00321

2
[ 635-80-3 ]
[ 108166-01-4 ]

Reference： [1]Journal of general chemistry of the USSR,1987,vol. 57,p. 96 - 99
Zhurnal Obshchei Khimii,1987,vol. 57,p. 113 - 117

Yield	Reaction Conditions	Operation in experiment
1: 70% 2: 18%	Stage #1: pentacarbonyl(1-[N-(4-methoxycarbonyl-2-ethenylphenyl)amino]ethylidene)chromium In hexane for 6h; Heating; Stage #2: With air for 14h;

4
[ 108166-01-4 ]
[ 73013-69-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: ammonium hydroxide / methanol / 12 h / 45 °C 2: triethylamine; trifluoroacetic anhydride / chloroform / 1.5 h / 10 °C
	Multi-step reaction with 2 steps 1: ammonium hydroxide / methanol / 12 h / 45 °C 2: trifluoroacetic anhydride; triethylamine / chloroform / 1.5 h / 10 °C

Reference： [1]Current Patent Assignee: ALEMBIC PHARMACEUTICALS LIMITED - WO2013/144737, 2013, A2
[2]Current Patent Assignee: ALEMBIC PHARMACEUTICALS LIMITED - US2015/57309, 2015, A1

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Code	Phrase
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P350	Gently wash with plenty of soap and water.
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P391	Collect spillage. Hazardous to the aquatic environment
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P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
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H226	Flammable liquid and vapour
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H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
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Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
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H336	May cause drowsiness or dizziness
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H341	Suspected of causing genetic defects
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H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
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H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 108166-01-4 ]

Quality Control of [ 108166-01-4 ]

Related Doc. of [ 108166-01-4 ]

Product Details of [ 108166-01-4 ]

Calculated chemistry of of [ 108166-01-4 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 108166-01-4 ]

Application In Synthesis of [ 108166-01-4 ]

[ 108166-01-4 ] Synthesis Path-Upstream 1~6

[ 108166-01-4 ] Synthesis Path-Downstream 1~4

Related Functional Groups of [ 108166-01-4 ]

Esters

Related Parent Nucleus of [ 108166-01-4 ]

Quinolines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 108166-01-4 ]

Related Parent Nucleus of
[ 108166-01-4 ]