Acetic Acid → HCID 178498263, compound

HRID 380412Notes

Reaction equation

HRID 380412 reaction equation
[NH2:1][C:2]1[C:11]([NH2:12])=[C:10]([O:13][CH3:14])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C(O)(=O)C.[CH3:19][O:20][C:21](OC)(OC)OC>CO.[OH-].[Na+].O>[CH3:19][O:20][C:21]1[NH:1][C:2]2[C:3]([C:4]([O:6][CH3:7])=[O:5])=[CH:8][CH:9]=[C:10]([O:13][CH3:14])[C:11]=2[N:12]=1

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 74613Tetramethyl orthocarbonateHCID 22663264Benzoic acid, 2,3-diamino-4-methoxy-, methyl ester (9CI)

Product 1

HCID 178498263HCID 178498263, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of methyl 2,3-diamino-4-methoxybenzoate [0.5 g, Reference Example 8(a)] acetic acid (0.15 ml) and tetramethoxymethane (0.53 ml) was stirred at 80° C. for 40 minutes. After cooling to room temperature the reaction mixture was diluted with a mixture of methanol (3.6 ml), 1N sodium hydroxide (2.55 ml) and water (8 ml). The resulting precipitate was filtered and then passed through a short filtration silica gel column to give the title compound (0.49 g) as a tan coloured solid. M+236. NMR (CDCl3): δ 3.93(s,3H), 4.05(s,3H), 4.23(s,3H), 6.69(d,J=8 Hz,1H), 7.74(d,J=8 Hz,1H). 9.48(bs,1H)]

Workup

  1. temperatureAfter cooling to room temperature the reaction mixture
  2. filtrationThe resulting precipitate was filtered
  3. filtrationpassed through a short filtration silica gel column

Sources & evidence

ORD record
ord-6e5ac6d15caa45eaba1a19c65569b8f3
Source dataset
uspto-grants-2001_10
Patent number
US06303600B1

Reaction notes

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