HCID 13606798, compound → HCID 13606799, compound

HRID 652737Notes

Reaction equation

HRID 652737 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH3:22])=[CH:7][N:8]3[C:15](=[O:16])[C:14]([C:17]([O:19]CC)=[O:18])=[CH:13][N:12]=[C:9]32)=[CH:4][CH:3]=1>C(O)(=O)C.Cl.O>[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH3:22])=[CH:7][N:8]3[C:15](=[O:16])[C:14]([C:17]([OH:19])=[O:18])=[CH:13][N:12]=[C:9]32)=[CH:4][CH:3]=1

Participants

5

Reactant 1

HCID 13606798HCID 13606798, compound

Product 1

HCID 13606799HCID 13606799, compoundYield 74.5%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolvent2×HCID 313Hydrochloric AcidSolvent2×HCID 962WaterSolvent

Procedure

A suspension of ethyl 10-amino-7-methyl-4-oxo-4H-pyrimido[2,1-a]isoquinoline-3-carboxylate (400 mg) in a mixture of acetic acid (6 ml) and 36% hydrochloric acid (3 ml) was refluxed for 55 minutes. The mixture was cooled and diluted with water. The precipitated solid obtained was collected and dissolved into 6 ml of 1N aqueous sodium hydroxide. The resulting solution was filtered for removal of insoluble materials. The filtrate obtained was cooled and adjusted to pH 6 with 1N hydrochloric acid and neutralized with acetic acid to give 10-amino-7-methyl-4-oxo-4H-pyrimido[2,1-a]isoquinoline-3-carboxylic acid (270 mg).

Workup

  1. temperaturewas refluxed for 55 minutes
  2. temperatureThe mixture was cooled
  3. customThe precipitated solid obtained
  4. customwas collected
  5. dissolutiondissolved into 6 ml of 1N aqueous sodium hydroxide
  6. filtrationThe resulting solution was filtered for removal of insoluble materials
  7. customThe filtrate obtained
  8. temperaturewas cooled

Sources & evidence

ORD record
ord-357f07444e554c2da7f4642ae836c10e
Source dataset
uspto-grants-1987_06
Patent number
US04673676

Reaction notes

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