5-Amino-2-chlorobenzoic acid → HCID 14988369, compound

HRID 728560Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[C:12]([C:16]1[CH:17]=[C:18]([CH:22]=[C:23]([C:26]([CH3:29])([CH3:28])[CH3:27])[C:24]=1[OH:25])[C:19](Cl)=[O:20])([CH3:15])([CH3:14])[CH3:13]>COCCOC>[C:7]([C:6]1[CH:10]=[C:2]([NH:1][C:19](=[O:20])[C:18]2[CH:22]=[C:23]([C:26]([CH3:27])([CH3:28])[CH3:29])[C:24]([OH:25])=[C:16]([C:12]([CH3:15])([CH3:14])[CH3:13])[CH:17]=2)[CH:3]=[CH:4][C:5]=1[Cl:11])([OH:9])=[O:8]

Participants

Conditions

Temperature: 25 °C

Procedure

A suspension of 6.90 g (0.04 mole) of 5-amino-2-chlorobenzoic acid in 100 ml of 1,2-dimethoxyethane was mixed with a solution of 5.08g (0.02 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 about 72 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 twice from a mixture of ethanol and water to give 2.8g of off-white solid N-(3-carboxy-4-chlorophenyl)-3,5-di-t-butyl-4-hydroxybenzamide, m.p. 265°-267° C. Analysis: Calculated for C22H26NO4Cl: %C, 65.4; %H, 6.5; %N, 3.4; Found: %C, 65.8; %H, 6.6; %N, 3.5.

Workup

temperatureThe reaction mixture was heated gently for 30 minutes
temperatureto cool
filtrationbefore being filtered
customto remove the hydrochloride salt of the excess starting amine
concentrationThe filtrate was concentrated under vacuum
additiondiluted with water
customThe resulting precipitate was collected
customwas then recrystallized twice from a mixture of ethanol and water

Sources & evidence

ORD record: ord-28fcc7c12c42445ca9add1eca26892e4
Source dataset: uspto-grants-1991_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05049572

Reaction notes

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