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

HRID 236387Notes

Reaction equation

HRID 236387 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-benzisoxazole (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-fd5d503284ef4cd495d14e6f9a20e559
Source dataset
uspto-grants-1987_02
Patent number
US04644064

Reaction notes

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