2-(1,1-Dimethylprop-2-ynyloxy)-4-nitrobenzonitrile → 2,2-Dimethyl-5-nitro-2H-chromene-8-carbonitrile

HRID 751041Notes

Reaction equation

HRID 751041 reaction equation
[CH3:1][C:2]([CH3:17])([O:5][C:6]1[CH:13]=[C:12]([N+:14]([O-:16])=[O:15])[CH:11]=[CH:10][C:7]=1[C:8]#[N:9])[C:3]#[CH:4]>C(N(CC)C1C=CC=CC=1)C>[CH3:1][C:2]1([CH3:17])[CH:3]=[CH:4][C:13]2[C:6](=[C:7]([C:8]#[N:9])[CH:10]=[CH:11][C:12]=2[N+:14]([O-:16])=[O:15])[O:5]1

Participants

3

Reactant 1

HCID 597543432-(1,1-Dimethylprop-2-ynyloxy)-4-nitrobenzonitrile

Product 1

HCID 597542382,2-Dimethyl-5-nitro-2H-chromene-8-carbonitrileYield 85.4%

Reagents, catalysts & solvents 1

HCID 7061N,N-DiethylanilineSolvent

Procedure

A solution of compound 6A (270 mg, 1.17 mmol) in N,N-diethylaniline (1 mL) was heated to 185° C. for 3 h. After cooling to rt, the reaction mixture was chromatographed (silica gel) eluting with 0-50% EtOAc/hexane to afford the title compound (230 mg).

Workup

  1. customthe reaction mixture was chromatographed (silica gel)
  2. washeluting with 0-50% EtOAc/hexane

Sources & evidence

ORD record
ord-5595700f4eff4fc0b82a6fa48e72c16a
Source dataset
uspto-grants-2008_07
Patent number
US07405234B2

Reaction notes

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