Acetic Acid → HCID 23445160, compound

HRID 433581Notes

Reaction equation

HRID 433581 reaction equation
[Cl: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].O>[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[F:9]

Participants

7

Reactant 4

HCID 176Acetic Acid2×HCID 97083-Chloro-4-fluoroanilineHCID 31214Ethyl orthoformate2×HCID 69379Ethyl nitroacetate

Product 1

HCID 23445160HCID 23445160, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

3-Chloro-4-fluoroaniline 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 with BH3 THF complex followed by hydrolytic workup and the title compound, Mp. 130-135° C. (H2O), MS: m/e=226 (M+), was obtained as an off-white crystalline solid.

Sources & evidence

ORD record
ord-2988a13524434c01ab2eaeac5e75a7a6
Source dataset
uspto-grants-2003_12
Patent number
US06667335B2

Reaction notes

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