Acetic Acid → HCID 23445023, compound

HRID 433623Notes

Reaction equation

HRID 433623 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].C([O:16][CH2:17][CH3:18])(OCC)OCC.[N+:19]([CH2:22]C(OCC)=O)([O-])=O.[C:28](O)(=O)C>[Fe]>[Cl:1][C:2]1[CH:3]=[C:4]([N:5]2[CH:28]=[C:18]([CH2:17][OH:16])[N:19]=[CH:22]2)[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 176Acetic Acid2×HCID 79323-ChloroanilineHCID 31214Ethyl orthoformate2×HCID 69379Ethyl nitroacetate

Product 1

HCID 23445023HCID 23445023, compound

Reagents, catalysts & solvents 1

HCID 23925IronCatalyst

Procedure

Following the general, method described in example 293, 3-chloroaniline 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 an off-white crystalline solid. Mp. 78-79° C. (H2O), MS: m/e=209 (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-36484880df8c4b818899691c3971570f
Source dataset
uspto-grants-2003_12
Patent number
US06667335B2

Reaction notes

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