HCID 13606822, compound → HCID 13606823, compound
Reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([Br:22])=[C:6]2[C:11]=1[C:10]1=[N:12][CH:13]=[C:14]([C:17]([O:19]CC)=[O:18])[C:15](=[O:16])[N:9]1[CH:8]=[CH:7]2>C(O)(=O)C.Cl.O>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([Br:22])=[C:6]2[C:11]=1[C:10]1=[N:12][CH:13]=[C:14]([C:17]([OH:19])=[O:18])[C:15](=[O:16])[N:9]1[CH:8]=[CH:7]2Participants
5
Reactant 1
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 80 °C
Procedure
A suspension of ethyl 11-amino-8-bromo-4-oxo-4H-pyrimido[2,1-a]isoquinoline-3-carboxylate (500 mg), in a mixture of acetic acid (25 ml) and 36% hydrochloric acid (5 ml) was heated at 80° C. for 3 hours. The mixture was cooled and diluted with water. The precipitated solid obtained was collected and dissolved into N,N-dimethylformamide (30 ml). The solution was added to an aqueous sodium bicarbonate solution (15 ml). The resulting precipitate was collected, and then dissolved in N,N-dimethylformamide (130 ml). The solution was filtered for removal of insoluble materials. The filtrate obtained was acidified with acetic acid to give 11-amino-8-bromo-4-oxo-4H-pyrimido[2,1-a]isoquinoline-3-carboxylic acid (180 mg).
Workup
- temperatureThe mixture was cooled
- customThe precipitated solid obtained
- customwas collected
- dissolutiondissolved into N,N-dimethylformamide (30 ml)
- additionThe solution was added to an aqueous sodium bicarbonate solution (15 ml)
- customThe resulting precipitate was collected
- dissolutiondissolved in N,N-dimethylformamide (130 ml)
- filtrationThe solution was filtered for removal of insoluble materials
- customThe filtrate obtained
Sources & evidence
- ORD record
- ord-14a890daadbc476aa4fcdfc27bae5277
- Source dataset
- uspto-grants-1987_06
- Patent number
- US04673676
Reaction notes
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