Acetic Acid → HCID 23445209, compound

HRID 433579Notes

Reaction equation

HRID 433579 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[CH3:9])[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]>[Cl: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[CH3:9]

Participants

6

Reactant 4

HCID 176Acetic Acid2×HCID 72553-Chloro-4-methylanilineHCID 31214Ethyl orthoformate2×HCID 69379Ethyl nitroacetate

Product 1

HCID 23445209HCID 23445209, compound

Reagents, catalysts & solvents 1

HCID 23925IronCatalyst

Procedure

According to example 234, 3-chloro-4-methylaniline (21.5 g, 150 mmol) 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 (10.0 g) 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 (5.2 g, 16%). Mp. 126-133° C. (AcOEt/hexane), MS: m/e=222 (M+)

Sources & evidence

ORD record
ord-42ca5e19b37240eeb31761198782d845
Source dataset
uspto-grants-2003_12
Patent number
US06667335B2

Reaction notes

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