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[ CAS No. 306937-12-2 ]

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2D
Chemical Structure| 306937-12-2
Chemical Structure| 306937-12-2
Structure of 306937-12-2 *Storage: {[proInfo.prStorage]}

Quality Control of [ 306937-12-2 ]

Related Doc. of [ 306937-12-2 ]

SDS

Product Details of [ 306937-12-2 ]

CAS No. :306937-12-2MDL No. :MFCD01765428
Formula : C13H17NO5 Boiling Point : 364.8±32.0°C at 760 mmHg
Linear Structure Formula :-InChI Key :HJRQIHYNWZEWHF-UHFFFAOYSA-N
M.W :267.28Pubchem ID :2735632
Synonyms :

Computed Properties of [ 306937-12-2 ]

TPSA : 84.9 H-Bond Acceptor Count : 5
XLogP3 : 2 H-Bond Donor Count : 2
SP3 : 0.38 Rotatable Bond Count : 5

Safety of [ 306937-12-2 ]

Signal Word:WarningClassN/A
Precautionary Statements:P261-P305+P351+P338UN#:N/A
Hazard Statements:H302-H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 306937-12-2 ]

  • Upstream synthesis route of [ 306937-12-2 ]
  • Downstream synthetic route of [ 306937-12-2 ]

[ 306937-12-2 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 24424-99-5 ]
  • [ 2840-26-8 ]
  • [ 306937-12-2 ]
YieldReaction ConditionsOperation in experiment
65% With sodium hydroxide In tetrahydrofuran at 20℃; for 12.50 h; Cooling with ice 3-Amino-p-anisic acid (1) (20.0 g,119 mmol)was suspended in asolution of NaOH (1 mol/L, 180 mL) and THF (150 mL). The mixturewas cooled in an ice bath. A solution of di-tert-butyl dicarbonate(Boc)2O (104.4 g, 479 mmol) in THF (70 mL) was then addeddropwise over a period of 30 min under stirring. The ice-bath wasremoved after dropping and the mixture was stirred for another12 h at room temperature. Thereafter, the THF was removed invacuo, and the remaining aqueous solution was diluted with water.The resulting mixture was extracted three times with AcOEt(70mL 3). The aqueous layer was acidified with concentrated HClto neutralize PH to 4e5 and extracted with AcOEt (80 mL 3). Thecombined organic layers were washed with water, and dried overNa2SO4. Then filtration and concentration in vacuo gave (2) (20.78 g,65percent) as off-white solid, which was used for the next step withoutfurther purification.
65% With sodium hydroxide In tetrahydrofuran at 20℃; for 5.00 h; Cooling with ice 20 g of 3-amino-4-methoxybenzoic acid (Compound 1) was dissolved in 180 ml of sodium hydroxide solution, 150 ml of tetrahydrofuran was added thereto, and a solution of BOC anhydride (104,4 g) in tetrahydrofuran (70 ml) was added dropwise to the ice bath The ice bath was removed and stirred at room temperature for 5 hours. After the completion of the stirring, the product was extracted with 80 ml of ethyl acetate, and the organic phase was combined and washed with saturated sodium chloride, and the mixture was washed with anhydrous sulfuric acid Sodium dry.Rotate the liquid to give 20.78 g of an off-white solid 3 - ((tert-butoxycarbonyl) amino) -4-methoxybenzoic acid (Compound 2) in 65percent yield;
50%
Stage #1: With sodium hydroxide In water at 50℃;
Stage #2: With hydrogenchloride In water
1) 1.0 g (6 mmol) 3-amino-4-methoxybenzoic acid is dissolved in 10 ml 4N NaOH aqueous solution, 2.5 ml (11 mmol) tert-butyric anhydride is slowly dropped into the solution. The mixture is heated up to 50° C. until the reaction finishes and the resulted alkaline solution is quickly acidified to pH=2 using 1 N hydrochloric acid and extracted three times using chloroform. The chloroform extract is pooled and desiccated with anhydrate sodium sulfate, subsequently condensed to dryness to obtain 0.8 g off- white solid, yield: 50percent.
Reference: [1] European Journal of Organic Chemistry, 2001, # 2, p. 311 - 322
[2] European Journal of Medicinal Chemistry, 2015, vol. 103, p. 80 - 90
[3] Patent: CN104817489, 2017, B. Location in patent: Paragraph 0037-0040
[4] Patent: US2011/178108, 2011, A1. Location in patent: Page/Page column 17
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