3-Aminobenzoic Acid → HCID 14988366, compound

HRID 728556Notes

Reaction equation

HRID 728556 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].[C:11]([C:15]1[CH:16]=[C:17]([CH:21]=[C:22]([C:25]([CH3:28])([CH3:27])[CH3:26])[C:23]=1[OH:24])[C:18](Cl)=[O:19])([CH3:14])([CH3:13])[CH3:12]>COCCOC>[C:5]([C:4]1[CH:3]=[C:2]([NH:1][C:18](=[O:19])[C:17]2[CH:21]=[C:22]([C:25]([CH3:26])([CH3:27])[CH3:28])[C:23]([OH:24])=[C:15]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:16]=2)[CH:10]=[CH:9][CH:8]=1)([OH:7])=[O:6]

Participants

4

Reactant 2

HCID 74193-Aminobenzoic AcidHCID 37871873,5-Di-tert-butyl-4-hydroxybenzoyl chloride

Product 1

HCID 14988366HCID 14988366, compoundYield 50.9%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Conditions

Temperature
25 °C

Procedure

A solution of 8.6g (0.063 mole) of m-aminobenzoic acid in 200 ml of 1,2-dimethoxyethane was mixed with a suspension of 8.0g (0.0298 mole) of 3,5-di-t-butyl-4-hydroxybenzoyl chloride in 100 ml of 1,2-dimethoxyethane, and the mixture was stirred at 25° C. for one hour. The reaction mixture was then filtered. The filtrate was thereafter diluted with 300 ml of water and cooled to give the crude product as a white solid. This material was recrystallized from a mixture of ethanol and water to give 5.6g of white solid N-(3-carboxyphenyl)-3,5-di-t-butyl-4-hydroxybenzamide, m.p. 279-280° C. Analysis: Calculated for C22H27NO4 : %C, 71.5; %H, 7.4; %N, 3.8; Found: %C, 72.0; %H, 7.3; %N, 3.7.

Workup

  1. filtrationThe reaction mixture was then filtered
  2. additionThe filtrate was thereafter diluted with 300 ml of water
  3. temperaturecooled
  4. customto give the crude product as a white solid
  5. customThis material was recrystallized from a mixture of ethanol and water

Sources & evidence

ORD record
ord-592918733abf4ee9a66f864248074643
Source dataset
uspto-grants-1991_09
Patent number
US05049572

Reaction notes

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