Hydrochloric Acid → 10-carboxy-5-(3-pyridylmethyl)-4H-pyrido [3,2,1-jk]carbazole-4-one
Reaction equation
[OH-].[Na+].BrBr.[C:5]([C:8]1[CH:9]=[CH:10][C:11]2[N:12]3[CH:23]=[C:22]([CH2:24][C:25]4[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=4)[C:21](=[O:31])[C:14]4[CH:15]=[CH:16][CH:17]=[C:18]([C:19]=2[CH:20]=1)[C:13]3=4)(=[O:7])C.S([O-])([O-])=[O:33].[Na+].[Na+].Cl>O.O1CCOCC1.CCOCC>[C:5]([C:8]1[CH:9]=[CH:10][C:11]2[N:12]3[CH:23]=[C:22]([CH2:24][C:25]4[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=4)[C:21](=[O:31])[C:14]4[CH:15]=[CH:16][CH:17]=[C:18]([C:19]=2[CH:20]=1)[C:13]3=4)([OH:33])=[O:7]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 3
Procedure
Sodium hydroxide (300 mg) was dissolved in water (15 ml), and bromine (0.1 ml) was added dropwise to the solution in an ice bath. The solution was diluted with dioxane (14 ml). 10-acetyl-5- (3-pyridylmethyl) -4H-pyrido [3,2,1-jk]carbazole-4-one (190 mg) produced in Example 194 was dissolved in dioxane (30 ml), and the solution that had been prepared as described above was added dropwise to this solution in an ice bath. After stirring for 5 minutes, sodium sulfite (70 mg) dissolved in water (10 ml) was added to the solution, and ether was added for phase separation. The aqueous layer was adjusted to pH 7 by adding 1N hydrochloric acid, and the crystals precipitated were recovered by filtration and washed with methanol and acetone in succession to obtain the title compound (67 mg, 35%).
Workup
- customthe solution that had been prepared
- additionabove was added dropwise to this solution in an ice bath
- additionwas added for phase separation
- customthe crystals precipitated
- filtrationwere recovered by filtration
- washwashed with methanol and acetone in succession
Sources & evidence
- ORD record
- ord-832eb809dcef4732958594b37bfba727
- Source dataset
- uspto-grants-2001_03
- Patent number
- US06197768B1
Reaction notes
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