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

HRID 728561Notes

Reaction equation

HRID 728561 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>[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

4

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 1

HCID 80711,2-DimethoxyethaneSolvent2×

Conditions

Temperature
25 °C

Procedure

A solution of 5.06g (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 6.69g (0.04 mole) of 3-amino-4-methoxybenzoic acid in 125 ml of 1,2-dimethoxyethane, 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 1.9g 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-6b3f22516be44bd697f937c6219dabe1
Source dataset
uspto-grants-1991_09
Patent number
US05049572

Reaction notes

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