Acetic Acid → HCID 23444998, compound

HRID 397931Notes

Reaction equation

HRID 397931 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-18040c8af5bc4c98b8bc39dfcaf7a4a9
Source dataset
uspto-grants-2003_08
Patent number
US06610723B2

Reaction notes

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