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

HRID 2351288Notes

Reaction equation

HRID 2351288 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-439a0d740b764356afeaaca6c825267b
Source dataset
uspto-grants-1989_10
Patent number
US04873234

Reaction notes

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