4-Aminophenol → HCID 22632923, compound

HRID 2270170Notes

Reaction equation

[Li]CCCC.C(NC(C)C)(C)C.[OH:13][C:14]1[CH:20]=[CH:19][C:17]([NH2:18])=[CH:16][CH:15]=1.F[C:22]1[CH:30]=[C:29]([F:31])[C:28]([F:32])=[CH:27][C:23]=1[C:24]([OH:26])=[O:25]>>[OH:13][C:14]1[CH:20]=[CH:19][C:17]([NH:18][C:22]2[CH:30]=[C:29]([F:31])[C:28]([F:32])=[CH:27][C:23]=2[C:24]([OH:26])=[O:25])=[CH:16][CH:15]=1

Participants

Reactant 4

HCID 4034-Aminophenol

HCID 7912Diisopropylamine

HCID 5211702,4,5-Trifluorobenzoic acid

HCID 178418339Butyllithium

Product 1

HCID 22632923HCID 22632923, compoundYield 99.8%

Procedure

Using General Method 1, the reaction of 2.5 M solution of n-BuLi in hexanes (29 mL, 73 mmol), diisopropylamine (9.5 mL, 68 mmol), 4-hydroxyaniline (1.85 g, 17 mmol), and 2,4,5-trifluorobenzoic acid (3 g, 17 mmol) provided 4.5 g of the crude title compound.

Sources & evidence

ORD record: ord-749085ae06a34e0b89b58925feeb129c
Source dataset: uspto-grants-2001_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06331538B1

Reaction notes

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