3-Amino-1,2-benzisoxazole-6-carbonitrile → 3-Amino-1,2-benzisoxazole-6-methanamine

HRID 842711Notes

Reaction equation

HRID 842711 reaction equation
CSC.B.[NH2:5][C:6]1[C:10]2[CH:11]=[CH:12][C:13]([C:15]#[N:16])=[CH:14][C:9]=2[O:8][N:7]=1>COCCOC>[NH2:5][C:6]1[C:10]2[CH:11]=[CH:12][C:13]([CH2:15][NH2:16])=[CH:14][C:9]=2[O:8][N:7]=1

Participants

4

Reactant 2

HCID 114578353-Amino-1,2-benzisoxazole-6-carbonitrileHCID 12423031(Dimethyl sulfide)trihydroboron

Product 1

HCID 220647313-Amino-1,2-benzisoxazole-6-methanamine

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

Borane methylsulfide complex (2 M in THF, 1.98 mL) was added to a stirred refluxing solution of 3-amino-6-cyano-1,2-benzisoxazole (210 mg, 1.32 mmol) in DME (10 mL). After 45 min excess methyl sulfide was evaporated and the reaction mixture was cooled and quenched with 1M HCl solution (10 mL). The mixture was stirred for 30 min and then was neutralised with sodium bicarbonate solution and concentrated to dryness. The residue was triturated with 5% methanol/chloroform, filtered and the filtrate evaporated in vacuo. The residue was purified by chromatography on silica (5% methanol, chloroform/ammonia) to give the title compound as a yellow solid:

Workup

  1. customAfter 45 min excess methyl sulfide was evaporated
  2. temperaturethe reaction mixture was cooled
  3. customquenched with 1M HCl solution (10 mL)
  4. concentrationconcentrated to dryness
  5. customThe residue was triturated with 5% methanol/chloroform
  6. filtrationfiltered
  7. customthe filtrate evaporated in vacuo
  8. customThe residue was purified by chromatography on silica (5% methanol, chloroform/ammonia)

Sources & evidence

ORD record
ord-e4eec364c1a5477e91952c71dc66b658
Source dataset
uspto-grants-2002_04
Patent number
US06376499B1

Reaction notes

Loading…