Dimethylformamide dimethyl acetal → HCID 57787980, compound

HRID 249961Notes

Reaction equation

HRID 249961 reaction equation
[NH2:1][C:2]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[C:7]([Br:13])=[CH:6][C:3]=1[C:4]#[N:5].CO[CH:16](OC)[N:17]([CH3:19])[CH3:18]>>[Br:13][C:7]1[C:8]([N+:10]([O-:12])=[O:11])=[CH:9][C:2]([N:1]=[CH:16][N:17]([CH3:19])[CH3:18])=[C:3]([C:4]#[N:5])[CH:6]=1

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 57423043HCID 57423043, compound

Product 1

HCID 57787980HCID 57787980, compoundYield 86%

Procedure

2-Amino-5-bromo-4-nitrobenzonitrile (815 mg, 3.37 mmol) is admixed with N,N-dimethylformamide dimethyl acetal (1.65 mL, 12.5 mmol). After 20 minutes in an ultrasonic bath, excess N,N-dimethylformamide dimethyl acetal is removed on a rotary evaporator to leave, after chromatographic purification of the residue (silica gel, n-hexane/ethyl acetate: 0→60% ethyl acetate) the product in 86% yield (863 mg).

Workup

  1. customexcess N,N-dimethylformamide dimethyl acetal is removed on a rotary evaporator
  2. customto leave
  3. customafter chromatographic purification of the residue (silica gel, n-hexane/ethyl acetate: 0→60% ethyl acetate) the product in 86% yield (863 mg)

Sources & evidence

ORD record
ord-2e96d0716d3f4d01b5e57d57a5dcc017
Source dataset
uspto-grants-2011_01
Patent number
US07863283B2

Reaction notes

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