Acetic Acid → HCID 23444964, compound

HRID 397921Notes

Reaction equation

HRID 397921 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[F:9])[NH2:5].C([O:17][CH2:18][CH3:19])(OCC)OCC.[N+:20]([CH2:23]C(OCC)=O)([O-])=O.[C:29](O)(=O)C>[Fe]>[Br:1][C:2]1[CH:3]=[C:4]([N:5]2[CH:29]=[C:19]([CH2:18][OH:17])[N:20]=[CH:23]2)[CH:6]=[CH:7][C:8]=1[F:9]

Participants

6

Reactant 4

HCID 176Acetic Acid2×HCID 31214Ethyl orthoformate2×HCID 69379Ethyl nitroacetateHCID 27792863-Bromo-4-fluoroaniline

Product 1

HCID 23444964HCID 23444964, compound

Reagents, catalysts & solvents 1

HCID 23925IronCatalyst

Procedure

Following the general method described in example 293, 3-bromo-4-fluoroaniline (K. S. Y. Lau et al., J. Org. Chem., 1981, 46, 2280-6) 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. Mp. 151-152° C. (H2O), MS: m/e=270 (M+).

Workup

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

Sources & evidence

ORD record
ord-b157d78227764f42839ae8ede5b16a5f
Source dataset
uspto-grants-2003_08
Patent number
US06610723B2

Reaction notes

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