2-[(Isopropylidenamino)oxy]-6-methoxymethoxybenzonitrile → 3-Aminobenzo[d]isoxazol-4-ol

HRID 1087728Notes

Reaction equation

HRID 1087728 reaction equation
C(=[N:4][O:5][C:6]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14]COC)[C:7]=1[C:8]#[N:9])(C)C>CO>[NH2:9][C:8]1[C:7]2[C:10]([OH:14])=[CH:11][CH:12]=[CH:13][C:6]=2[O:5][N:4]=1

Participants

3

Reactant 1

HCID 148362012-[(Isopropylidenamino)oxy]-6-methoxymethoxybenzonitrile

Product 1

HCID 1357037053-Aminobenzo[d]isoxazol-4-olYield 89%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-[(Isopropylidenamino)oxy]-6-methoxymethoxybenzonitrile of Example 1(c) (9.91 g, 0.0423 mole) was dissolved in 100 ml of methanol and then 100 ml of freshly prepared saturated HCl-ether was added. After stirring overnight (about 16 hours) at room temperature the reaction mixture was concentrated under reduced pressure and the residue triturated with CH2Cl2 and filtered. Recrystallization from methanol-water gave 5.62 g (89%) of 3-amino-4-hydroxy-1,2-benzisoxazole, mp 255° (d).

Workup

  1. concentrationwas concentrated under reduced pressure
  2. customthe residue triturated with CH2Cl2
  3. filtrationfiltered
  4. customRecrystallization from methanol-water

Sources & evidence

ORD record
ord-8cf190a4a5ca42c98dc4e3b3b7bf498a
Source dataset
uspto-grants-1990_10
Patent number
US04960767

Reaction notes

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