Acetic Acid → HCID 23444998, compound

HRID 433626Notes

Reaction equation

HRID 433626 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1)[NH2:6].C([O:21][CH2:22][CH3:23])(OCC)OCC.[N+:24]([CH2:27]C(OCC)=O)([O-])=O.[C:33](O)(=O)C>[Fe]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:6]2[CH:33]=[C:23]([CH2:22][OH:21])[N:24]=[CH:27]2)[CH:7]=[C:8]([C:10]([F:11])([F:12])[F:13])[CH:9]=1

Participants

6

Reactant 4

HCID 176Acetic Acid2×HCID 31214Ethyl orthoformate2×HCID 69379Ethyl nitroacetateHCID 6056715-(Trifluoromethyl)-m-anisidine

Product 1

HCID 23444998HCID 23444998, compound

Reagents, catalysts & solvents 1

HCID 23925IronCatalyst

Procedure

Following the general method described in example 293, 3-methoxy-5-trifluoromethylaniline 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 light brown crystalline solid. Mp. 133-134° C. (H2O), MS: m/e=272 (M+).

Workup

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

Sources & evidence

ORD record
ord-41f5f07e48c84b70b4d9fb8be9824dcc
Source dataset
uspto-grants-2003_12
Patent number
US06667335B2

Reaction notes

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