Water → Procarbazine Hydrochloride
Reaction equation
Br.[CH:2]([NH:5][C:6](=[O:17])[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][NH:14][NH:15][CH3:16])=[CH:9][CH:8]=1)([CH3:4])[CH3:3].O.C(=O)([O-])[O-].[K+].[K+].C(Cl)[Cl:26]>>[ClH:26].[CH:2]([NH:5][C:6](=[O:17])[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][NH:14][NH:15][CH3:16])=[CH:9][CH:8]=1)([CH3:4])[CH3:3]Participants
Procedure
87.5 g. of 4-[(2-methyl-hydrazino)-methyl]-benzoic acid isopropylamide hydrobromide (obtained according to Example 3) were dissolved in 550 ml. of water. To this solution, there were added 1000 ml. of methylene chloride and, while cooling with ice and stirring under nitrogen atmosphere, 1200 g. of potassium carbonate portionwise. The methylene chloride layer was separated and the aqueous slurry extracted 3 times with 500 ml. of methylene chloride in a nitrogen atmosphere. The united methylene chloride extracts were concentrated in vacuo. The residue was dissolved under nitrogen in 100 ml. of methanol and treated, while cooling with ice, with 40 ml. of a 45% methanolic hydrochloric solution, which induces immediate crystallization. The crystals were filtered off and recrystallized from methanol, yielding 4-[(2-methyl-hydrazino)-methyl]-benzoic acid isopropylamide hydrochloride melting at 223°-226°.
Workup
- additionTo this solution, there were added 1000 ml
- customThe methylene chloride layer was separated
- extractionthe aqueous slurry extracted 3 times with 500 ml
- concentrationThe united methylene chloride extracts were concentrated in vacuo
- dissolutionThe residue was dissolved under nitrogen in 100 ml
- additionof methanol and treated
- temperaturewhile cooling with ice, with 40 ml
- customcrystallization
- filtrationThe crystals were filtered off
- customrecrystallized from methanol
Sources & evidence
- ORD record
- ord-4aef1caf460646dca8b4a681ac0b4b95
- Source dataset
- uspto-grants-1976_01
- Patent number
- US03931268
Reaction notes
Loading…