Ammonium Chloride → HCID 13606798, compound

HRID 652736Notes

Reaction equation

HRID 652736 reaction equation
[CH3:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([N+:12]([O-])=O)=[CH:9][CH:10]=2)[C:5]2=[N:15][CH:16]=[C:17]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:18](=[O:19])[N:4]2[CH:3]=1.[Cl-].[NH4+].C(Cl)(Cl)Cl.CO>O.C(O)C.[Fe]>[NH2:12][C:8]1[CH:7]=[C:6]2[C:11]([C:2]([CH3:1])=[CH:3][N:4]3[C:18](=[O:19])[C:17]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:16][N:15]=[C:5]32)=[CH:10][CH:9]=1

Participants

7

Reactant 3

HCID 25517Ammonium Chloride2×HCID 13606796HCID 13606796, compoundHCID 21584188Chloroform methanol

Product 1

HCID 13606798HCID 13606798, compoundYield 78.6%

Reagents, catalysts & solvents 3

HCID 23925IronCatalyst2×HCID 702EthanolSolventHCID 962WaterSolvent3×

Procedure

To a stirred mixture of ethyl 7-methyl-10-nitro-4-oxo-4H-pyrimido[2,1-a]isoquinoline-3-carboxylate (140 mg) and iron powder (90 mg) in a mixture of water (0.5 ml) and ethanol (13 ml) was added a solution of ammonium chloride (90 mg) in water (0.5 ml) under refluxing. After refluxing for 1 hour and 50 minutes, ammonium chloride (28 mg) in water (0.5 ml) and iron (50 mg) was added, and then the mixture was stirred for additional 1 hour. The reaction mixture was filtered and the residue on a filter was washed with hot ethanol. The filtrate was concentrated in vacuo and then treated with dilute sodium hydrogen carbonate solution to give crude product. Chromatography on silica gel with chloroform-methanol gave pure ethyl 10-amino-7-methyl-4-oxo-4H-pyrimido[2,1-a]isoquinoline-3-carboxylate (100 mg).

Workup

  1. temperatureunder refluxing
  2. temperatureAfter refluxing for 1 hour and 50 minutes
  3. filtrationThe reaction mixture was filtered
  4. washthe residue on a filter was washed with hot ethanol
  5. concentrationThe filtrate was concentrated in vacuo
  6. additiontreated with dilute sodium hydrogen carbonate solution
  7. customto give crude product

Sources & evidence

ORD record
ord-d79336918d3d43638a57fb3cc7b3172c
Source dataset
uspto-grants-1987_06
Patent number
US04673676

Reaction notes

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