Acetic Acid → HCID 23444975, compound

HRID 433612Notes

Reaction equation

HRID 433612 reaction equation
[F:1][C:2]([C:5]1[CH:6]=[C:7]([NH2:12])[CH:8]=[CH:9][C:10]=1[F:11])([F:4])[CH3:3].C([O:20][CH2:21][CH3:22])(OCC)OCC.[N+:23]([CH2:26]C(OCC)=O)([O-])=O.[C:32](O)(=O)C>[Fe]>[F:4][C:2]([C:5]1[CH:6]=[C:7]([N:12]2[CH:32]=[C:22]([CH2:21][OH:20])[N:23]=[CH:26]2)[CH:8]=[CH:9][C:10]=1[F:11])([F:1])[CH3:3]

Participants

6

Reactant 4

HCID 176Acetic Acid2×HCID 31214Ethyl orthoformate2×HCID 69379Ethyl nitroacetateHCID 23445006445303-18-4

Product 1

HCID 23444975HCID 23444975, compound

Reagents, catalysts & solvents 1

HCID 23925IronCatalyst

Procedure

Following the general method described in example 293, 3-(1,1-difluoro-ethyl)-4-fluoro phenylamine was reacted with triethyl orthoformate, ethyl nitroacetate and acetic acid followed by treatment with triethyl orthoformate, iron and acetic acid and subsequent alkaline hydrolysis. The isolated acid was directly reduced according to example 264, by reaction with BH3 THF complex followed by hydrolytic workup and the title compound was obtained as a white crystalline solid. MS: m/e=257 (M+H+).

Workup

  1. customThe isolated acid was directly reduced according to example 264, by reaction with BH3 THF complex

Sources & evidence

ORD record
ord-f1188ab20ce34d2fadaa2f74b3983d8f
Source dataset
uspto-grants-2003_12
Patent number
US06667335B2

Reaction notes

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