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Product Details of [ 36669-02-0 ]

CAS No. :36669-02-0 MDL No. :MFCD22490931
Formula : C10H10O5 Boiling Point : -
Linear Structure Formula :- InChI Key :BQGDDMMXPRJQHZ-UHFFFAOYSA-N
M.W : 210.18 Pubchem ID :12223651
Synonyms :

Safety of [ 36669-02-0 ]

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 [ 36669-02-0 ]

* 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 [ 36669-02-0 ]
  • Downstream synthetic route of [ 36669-02-0 ]

[ 36669-02-0 ] Synthesis Path-Upstream   1~10

  • 1
  • [ 37418-88-5 ]
  • [ 36669-02-0 ]
Reference: [1] Journal of the American Chemical Society, 1955, vol. 77, p. 5092,5094
[2] Patent: US6017919, 2000, A,
[3] Patent: WO2017/212329, 2017, A1,
[4] Patent: WO2008/115516, 2008, A2,
  • 2
  • [ 74-88-4 ]
  • [ 36669-02-0 ]
YieldReaction ConditionsOperation in experiment
1.9 g With sodium hydrogencarbonate In N,N-dimethyl-formamide at 55℃; for 3 h; A mixture of 3-hydroxyphtalic anhydride (1.6 g, 9.8 mmol) in MeOH (25 mL) was refluxed for 3 hours. The mixture was cooled to room temperature and concentrated. The residue and NaHC03 (2.3 g, 27.3 mmol) were stirred in DMF (20 mL). Methyl iodide (1.46 mL, 23.4 mmol) was added and the reaction mixture was heated at 55 °C for 3 hours. The reaction was cooled to room temperature and diluted with EtOAc (80 mL) and water (40 mL). The mixture was acidified with an aqueous solution of HCI (4N) and the aqueous layer was extracted with EtOAc (2 x 40 mL). The combined organic layers were washed with water (2 x 100 mL), brine (2 x 100 mL) and dried over MgS04. The solvent was removed in vacuo and the crude product was purified by flash column . chromatography with 3:7 EtOAc: Petrol to give 1 ,2-dimethyl 3-hydroxybenzene-1 ,2-dicarboxylate (1.9 g, 9.1 mmol, 94percent) as a pale pink oil. H NMR (400 MHz, DMSO-cf6) δ ppm 10.28 (s, 1 H), 7.44-7.30 (m, 2H), 7.17 (dd, J = 7.1 , 2.2 Hz, 1 H), 3.80 (s, 3H), 3.77 (s, 3H). 13C NMR (101 MHz, DMSO-d6) δ ppm 167.61 , 166.10, 155.04, 130.96, 129.04, 122.99, 120.92, 120.42, 52.90, 52.53. LC-MS: [M+H]+ = 211
Reference: [1] Patent: WO2017/212329, 2017, A1, . Location in patent: Page/Page column 20; 70
  • 3
  • [ 601-97-8 ]
  • [ 74-88-4 ]
  • [ 36669-02-0 ]
YieldReaction ConditionsOperation in experiment
77% With sodium hydrogencarbonate In N,N-dimethyl-formamide at 50 - 55℃; for 2 - 4 h; Example 3 4-Benzyloxy-2-(2,6-dioxo-piperidin-3-yl)-isoindole-l,3-dioneStep 1 :[169] A mixture of 3-hydroxyphthalic anhydride (4.96 g, 30.2 mmol) in methanol(60 mL) was refluxed for 3 h, cooled to room temperature, and the solvent was evaporated under vacuum. The residue and sodium bicarbonate (7.11 g, 84.6 mmol) were suspended in DMF (40 mL). Iodomethane (4.53 mL, 72.5 mmol) was added and the reaction mixture was heated at 50 0C for 2 h. The solvent was removed under vacuum and the residue was partitioned between ethyl acetate (120 mL) and water (100 mL). The organic phase was washed with water (2 x 100 mL) and evaporated. The residue was chromatographed using a hexanes-ethyl acetate gradient, eluting the product at 6:4 hexanes-ethyl acetate, 4.83 g of 3- hydroxy-phthalic acid dimethyl ester, in 76percent yield; 1H NMR (CDCl3) δ 3.89 (s, 3H), 3.92 (s, 3H), 6.97 (dd, J = 7.9 Hz, J = 0.9 Hz, IH), 7.09 (dd, J = 8.6 Hz, J = 1.0 Hz, IH), 7.46 (t, J = 8.3 Hz, IH), 10.58 (s, IH).
Example 242-(2,6-Dioxo-piperidin-3-yl)-4-(4-methoxy-benzyloxy)-isoindole-l,3-dioneStep 1 :[232] A stirred mixture of 3-hydroxyphthalic anhydride (20.5 g, 125 mmol) in methanol (100 mL) was heated to reflux for three hours. The solvent was evaporated in vacuo, and the residue was suspended in sodium bicarbonate (29.4 g, 350 mmol) in DMF (250 mL), followed by addition of iodomethane (19 mL, 300 mmol) and heating at 550C for four hours. The mixture was cooled to room temperature, solvent evaporated in vacuo, and <n="78"/>the residue was partitioned between water (200 mL) and ethyl acetate (200 mL). The organic layer was washed with water (2 x 200 mL), dried, concentrated in vauco, and then purified by flash column chromatography (Silica Gel, EtOAc/Hexane, 0percent gradient to 100percent 30 min) to give 3-hydroxyphthalic acid dimethyl ester (20.2 g, 77percent yield). The product was used in the next step without further purification.
Reference: [1] Patent: WO2008/115516, 2008, A2, . Location in patent: Page/Page column 52; 76-77
  • 4
  • [ 67-56-1 ]
  • [ 37418-88-5 ]
  • [ 36669-02-0 ]
Reference: [1] Journal of Medicinal Chemistry, 2018, vol. 61, # 2, p. 482 - 491
[2] Journal of the American Chemical Society, 1955, vol. 77, p. 5092,5094
[3] Chimia, 1996, vol. 50, # 11, p. 530 - 532
  • 5
  • [ 67-56-1 ]
  • [ 601-97-8 ]
  • [ 36669-02-0 ]
Reference: [1] European Journal of Medicinal Chemistry, 2017, vol. 137, p. 76 - 87
  • 6
  • [ 186581-53-3 ]
  • [ 16534-14-8 ]
  • [ 36669-02-0 ]
Reference: [1] Journal of the American Chemical Society, 1955, vol. 77, p. 5092,5094
  • 7
  • [ 496-64-0 ]
  • [ 762-42-5 ]
  • [ 36669-02-0 ]
Reference: [1] Chemische Berichte, 1987, vol. 120, p. 1347 - 1356
  • 8
  • [ 108298-54-0 ]
  • [ 36669-02-0 ]
Reference: [1] Chemische Berichte, 1987, vol. 120, p. 1347 - 1356
  • 9
  • [ 75232-81-4 ]
  • [ 762-42-5 ]
  • [ 36669-02-0 ]
Reference: [1] Journal of Organic Chemistry, 1980, vol. 45, # 23, p. 4810 - 4812
  • 10
  • [ 67609-49-8 ]
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Reference: [1] Chemistry Letters, 1978, p. 649 - 652
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