Acetic Acid → HCID 23445209, compound

HRID 397887Notes

Reaction equation

HRID 397887 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-07b35f4181c74a51b7388f2eb0740488
Source dataset
uspto-grants-2003_08
Patent number
US06610723B2

Reaction notes

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