Acetic Acid → HCID 23445088, compound

HRID 397936

Reaction equation

HRID 397936 reaction equation
[F:1][C:2]1([F:12])[O:6][C:5]2[CH:7]=[CH:8][C:9]([NH2:11])=[CH:10][C:4]=2[O:3]1.C([O:20][CH2:21][CH3:22])(OCC)OCC.[N+:23]([CH2:26]C(OCC)=O)([O-])=O.[C:32](O)(=O)C>[Fe]>[F:12][C:2]1([F:1])[O:6][C:5]2[CH:7]=[CH:8][C:9]([N:11]3[CH:32]=[C:22]([CH2:21][OH:20])[N:23]=[CH:26]3)=[CH:10][C:4]=2[O:3]1

Participants

6

Reactant 4

HCID 176Acetic Acid2×HCID 31214Ethyl orthoformate2×HCID 69379Ethyl nitroacetateHCID 27368935-Amino-2,2-difluoro-1,3-benzodioxole

Product 1

HCID 23445088HCID 23445088, compound

Reagents, catalysts & solvents 1

HCID 23925IronCatalyst

Procedure

Following the general method described in example 293, 2,2-difluoro-benzo[1,3]dioxol-5-ylamine 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 light brown solid. Mp. 163-164° C. (H2O), MS: m/e=254 (M+).

Workup

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

Sources & evidence

ORD record
ord-65ecd3d8357344cfb9ddc7bccd520302
Source dataset
uspto-grants-2003_08
Patent number
US06610723B2

Linked notes

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