3-Amino-4-methoxybenzoic acid → HCID 14988370, compound

HRID 1029842Notes

Reaction equation

HRID 1029842 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([C:15]([CH3:18])([CH3:17])[CH3:16])[C:13]=1[OH:14])[C:8](Cl)=[O:9])([CH3:4])([CH3:3])[CH3:2].[NH2:19][C:20]1[CH:21]=[C:22]([CH:26]=[CH:27][C:28]=1[O:29][CH3:30])[C:23]([OH:25])=[O:24]>COCCOC.CCCC>[C:23]([C:22]1[CH:26]=[CH:27][C:28]([O:29][CH3:30])=[C:20]([NH:19][C:8](=[O:9])[C:7]2[CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:13]([OH:14])=[C:12]([C:15]([CH3:18])([CH3:17])[CH3:16])[CH:11]=2)[CH:21]=1)([OH:25])=[O:24]

Participants

5

Reactant 2

HCID 178233-Amino-4-methoxybenzoic acidHCID 37871873,5-Di-tert-butyl-4-hydroxybenzoyl chloride

Product 1

HCID 14988370HCID 14988370, compoundYield 23.8%

Reagents, catalysts & solvents 2

HCID 7843ButaneSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 5.06 g (0.02 mole) of 3,5-di-t-butyl-4-hydroxybenzoyl chloride in 100 ml of 1,2-dimethoxyethane was mixed with a solution of 6.69 g (0.04 mole) of 3-amino-4-methoxybenzoic acid in 125 ml of 1,2-dimethyethane, and the mixture was stirred at 25° C. for about 16 hours. The reaction mixture was heated gently for 30 minutes and then allowed to cool before being filtered to remove the hydrochloride salt of the excess starting amine. The filtrate was concentrated under vacuum and then diluted with water. The resulting precipitate was collected and was then recrystallized three times from a mixture of ethanol and water to give 1.9 g of white solid N-(5-carboxy-2-methoxyphenyl)-3,5-di-t-butyl-4-hydroxybenzamide, m.p. 259°-261° C. Analysis: Calculated for C23H29NO5 : %C, 69.2; %H, 7.3; %N, 3.5; Found: %C, 69.3; %H, 7.3; %H, 3.6.

Workup

  1. temperatureThe reaction mixture was heated gently for 30 minutes
  2. temperatureto cool
  3. filtrationbefore being filtered
  4. customto remove the hydrochloride salt of the excess starting amine
  5. concentrationThe filtrate was concentrated under vacuum
  6. additiondiluted with water
  7. customThe resulting precipitate was collected
  8. customwas then recrystallized three times
  9. additionfrom a mixture of ethanol and water

Sources & evidence

ORD record
ord-e0cab052746d4b978ab0288044c57289
Source dataset
uspto-grants-1992_04
Patent number
US05103037

Reaction notes

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