P-Anisidine → HCID 22632869, compound

HRID 2416778Notes

Reaction equation

[Li]CCCC.C(NC(C)C)(C)C.[CH3:13][O:14][C:15]1[CH:21]=[CH:20][C:18]([NH2:19])=[CH:17][CH:16]=1.F[C:23]1[CH:31]=[C:30]([F:32])[C:29]([F:33])=[CH:28][C:24]=1[C:25]([OH:27])=[O:26]>>[CH3:13][O:14][C:15]1[CH:21]=[CH:20][C:18]([NH:19][C:23]2[CH:31]=[C:30]([F:32])[C:29]([F:33])=[CH:28][C:24]=2[C:25]([OH:27])=[O:26])=[CH:17][CH:16]=1

Participants

Reactant 4

HCID 7732P-Anisidine

HCID 7912Diisopropylamine

HCID 5211702,4,5-Trifluorobenzoic acid

HCID 178418339Butyllithium

Product 1

HCID 22632869HCID 22632869, compoundYield 120.5%

Procedure

Using General Method 1, the reaction of 2.5 M solution of n-BuLi in hexanes (26 mL, 64 mmol), diisopropylamine (8.7 mL, 62 mmol), 4-methoxy-aniline (2.6 g, 17 mmol), and 2,4,5-trifluorobenzoic acid (3.6 g, 20.7 mmol) provided 5.72 g of the crude title compound.

Sources & evidence

ORD record: ord-4682dc0367ac450593c3a15b4c7e18d2
Source dataset: uspto-grants-2004_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06825199B2

Reaction notes

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