Acetic Acid → HCID 23444967, compound

HRID 433627Notes

Reaction equation

HRID 433627 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:9]=[CH:10][CH:11]=1)[NH2:8])([CH3:4])([CH3:3])[CH3:2].C([O:19][CH2:20][CH3:21])(OCC)OCC.[N+:22]([CH2:25]C(OCC)=O)([O-])=O.[C:31](O)(=O)C>[Fe]>[C:1]([C:5]1[CH:6]=[C:7]([N:8]2[CH:31]=[C:21]([CH2:20][OH:19])[N:22]=[CH:25]2)[CH:9]=[CH:10][CH:11]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 176Acetic Acid2×HCID 31214Ethyl orthoformate2×HCID 69379Ethyl nitroacetateHCID 793343-tert-Butylaniline

Product 1

HCID 23444967HCID 23444967, compound

Reagents, catalysts & solvents 1

HCID 23925IronCatalyst

Procedure

Following the general method described in example 293, 3-tert-butylaniline 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 colorless oil. MS: m/e=230 (M+)

Workup

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

Sources & evidence

ORD record
ord-e1ff5b96e618462eaa97cf14e1405435
Source dataset
uspto-grants-2003_12
Patent number
US06667335B2

Reaction notes

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