Hydrochloric Acid → 6-(1-Ethoxy-carbonyl-ethylidenehydrazino)-beta-carboline-3-carboxylic acid ethyl ester
Reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][C:9]2[NH:10][C:11]3[C:16]([C:17]=2[CH:18]=1)=[CH:15][C:14]([NH2:19])=[CH:13][CH:12]=3)=[O:5])[CH3:2].Cl.[N:21]([O-])=O.[Na+].C(OC(=O)[CH:29]([CH3:33])[C:30](C)=[O:31])C.[OH-].[K+].[CH2:37]([OH:39])[CH3:38]>O>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][C:9]2[NH:10][C:11]3[C:16]([C:17]=2[CH:18]=1)=[CH:15][C:14]([N:19]([O:39][CH2:37][CH3:38])[N:21]=[CH:33][CH:29]=[C:30]=[O:31])=[CH:13][CH:12]=3)=[O:5])[CH3:2]Participants
Reactant 6
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 4 °C
Procedure
710 mg of 6-amino-β-carboline-3-carboxylic acid ethyl ester is mixed in 18 ml of water at 4° C. with 1.2 ml of concentrated hydrochloric acid. A solution of 210 mg of sodium nitrite in 20 ml of water is added in drops to the precipitated salt, and it is stirred for another 15 minutes at 4° C. This solution is added in drops at 4° C. to 410 mg of ethyl-2-methylacetoacetate and 1 ml of 50% KOH in 3 ml of ethanol and 6 ml of water, and it is stirred for another 3 hours. The reaction mixture is mixed with 50 ml of water and extracted with ethyl acetate. The organic phases are washed with water, dried, and concentrated by evaporation. 250 mg of 6-(1-ethoxy-carbonyl-ethylidenehydrazino)-β-carboline-3-carboxylic acid ethyl ester is obtained, which is processed without further purification.
Workup
- stirringis stirred for another 3 hours
- extractionextracted with ethyl acetate
- washThe organic phases are washed with water
- customdried
- concentrationconcentrated by evaporation
Sources & evidence
- ORD record
- ord-8380dc94f6f0411da6fad8d76ef93e8a
- Source dataset
- uspto-grants-2000_10
- Patent number
- US06127368
Reaction notes
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