Hydrazine hydrate (1:1) → HCID 20217199, compound

HRID 2296054Notes

Reaction equation

HRID 2296054 reaction equation
[Cl:1][C:2]1[C:10]2[O:9][N:8]=[C:7]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[F:17])[C:6]=2[CH:5]=[CH:4][C:3]=1[O:18][CH2:19][CH2:20][N:21]1C(=O)C2=CC=CC=C2C1=O.O.NN>CO>[ClH:1].[Cl:1][C:2]1[C:10]2[O:9][N:8]=[C:7]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[F:17])[C:6]=2[CH:5]=[CH:4][C:3]=1[O:18][CH2:19][CH2:20][NH2:21]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 13271933HCID 13271933, compound

Product 1

HCID 20217199HCID 20217199, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

7-Chloro-3-(2-fluorophenyl)-6-(2-phthalimidoethoxy)-1,2-benzisoxa zole (8.0 g) is heated under reflux for 4 hrs in 75 ml of methanol containing 1.3 g of 85% hydrazine hydrate. The solid is filtered and the methanol is evaporated. The combined solids are distributed between water and ethyl acetate. The organic phase is dried and concentrated under reduced pressure to give 5.30 g (87%) as a glass that crystallizes slowly. The hydrochloride forms smoothly in ether with a trace of methanol as crystals, mp 235°-240°. The analytical sample is recrystallized from propanol/methanol and has mp 240°-243°.

Workup

  1. filtrationThe solid is filtered
  2. customthe methanol is evaporated
  3. customThe organic phase is dried
  4. concentrationconcentrated under reduced pressure
  5. customto give 5.30 g (87%) as a glass
  6. customthat crystallizes slowly
  7. customThe analytical sample is recrystallized from propanol/methanol

Sources & evidence

ORD record
ord-c859101fe8e249bcad15fe595ce47c88
Source dataset
uspto-grants-1984_01
Patent number
US04427691

Reaction notes

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