2-Methyl-6-nitrobenzaldehyde → 4-Methyl-2,1-benzisoxazole

HRID 648451Notes

Reaction equation

HRID 648451 reaction equation
[CH3:1][C:2]1[C:7]([CH:8]=O)=[C:6]([N+:10]([O-:12])=O)[CH:5]=[CH:4][CH:3]=1>Cl.O>[CH3:1][C:2]1[C:7]2=[CH:8][O:12][N:10]=[C:6]2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 140982782-Methyl-6-nitrobenzaldehyde

Product 1

HCID 140982794-Methyl-2,1-benzisoxazoleYield 92.6%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

To a solution of 49.64 g (220 mmoles) stannous chloride dihydrate in 132 ml concentrated hydrochloric acid cooled to 15° was added 9.08 g (55.0 mmoles) of 6-methyl-2-nitrobenzaldehyde with rapid stirring. After 2 hours the mixture was diluted with 250 ml water and extracted with 3×150 ml ether. The extract was washed successively with dilute sodium bicarbonate solution, water, and brine, dried, and concentrated to give 6.78 g oil. The oil was flash chromatographed, eluting with chloroform to give 6.10 g (83%) (1) as an oil; nmr (deuteriochloroform): 2.5 (s, 3H), 6.7 (dd, 1H), 7.3 (m, 2H), 9.1 (s, 1H).

Workup

  1. extractionextracted with 3×150 ml ether
  2. washThe extract was washed successively with dilute sodium bicarbonate solution, water, and brine
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f41a05c2e90f45baaf2df4918400e22e
Source dataset
uspto-grants-1988_04
Patent number
US04735956

Reaction notes

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