Ammonia → HCID 20321574, compound

HRID 2397663Notes

Reaction equation

HRID 2397663 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH3:25])[N:10]=[CH:11][C:12]=2[CH2:13][N:14]2C(=O)C3=CC=CC=C3C2=O)=[C:4]([C:26](=O)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[F:33])[CH:3]=1.N>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]2[C:8]3[N:9]([CH3:25])[N:10]=[CH:11][C:12]=3[CH2:13][N:14]=[C:26]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[F:33])[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 20321555HCID 20321555, compound

Product 1

HCID 20321574HCID 20321574, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 0.33 g of 3-[4-chloro-2-(2-fluoro-benzoyl)-phenyl]-4-phthalimidomethyl-2-methyl-pyrazole in 20 ml of methanol is saturated with ammonia and allowed to stand at room temperature for 2 days. The residue obtained after removal of solvent is treated with water and then extracted with diethyl ether. The ether extract is washed with a diluted aqueous sodium hydroxide solution, water and a saturated solution of sodium chloride in water and dried over sodium sulfate. Removal of ether yields an oil which is then chromatographed on a column of silica gel, the material being eluted with ethyl acetate. The solid residue obtained after removal of ethyl acetate is crystallized from a mixture of ethyl acetate and petroleum ether to yield the 8-chloro-6-(2-fluorophenyl)-1-methyl-1H,4H-pyrazolo [4,3-d](2) benzazepine m.p. 127°-129°, which is identical with the compound prepared according to the process of example 2.

Workup

  1. customThe residue obtained
  2. customafter removal of solvent
  3. additionis treated with water
  4. extractionextracted with diethyl ether
  5. extractionThe ether extract
  6. washis washed with a diluted aqueous sodium hydroxide solution, water
  7. dry with materiala saturated solution of sodium chloride in water and dried over sodium sulfate
  8. customRemoval of ether
  9. customyields an oil which
  10. customis then chromatographed on a column of silica gel
  11. washthe material being eluted with ethyl acetate
  12. customThe solid residue obtained
  13. customafter removal of ethyl acetate
  14. customis crystallized from a mixture of ethyl acetate and petroleum ether

Sources & evidence

ORD record
ord-6b0ae4a0161f48ac8811918f6b53b9b0
Source dataset
uspto-grants-1977_05
Patent number
US04022801

Reaction notes

Loading…