Hydrochloric Acid → HCID 86748093, compound

HRID 1742930Notes

Reaction equation

HRID 1742930 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]([CH3:12])[C:7]3=[CH:13][C:14]([C:16]([OH:18])=[O:17])=[N:15][N:6]3[C:5](=[O:19])[C:4]=2[CH:3]=1.Cl.[CH2:21](O)[CH3:22]>>[NH2:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]([CH3:12])[C:7]3=[CH:13][C:14]([C:16]([O:18][CH2:21][CH3:22])=[O:17])=[N:15][N:6]3[C:5](=[O:19])[C:4]=2[CH:3]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 12724759HCID 12724759, compound

Product 1

HCID 86748093HCID 86748093, compoundYield 81%

Procedure

A mixture of 7-amino-4,9-dihydro-4-methyl-9-oxopyrazolo[5,1-b]quinazoline-2-carboxylic acid (8.03 g, 31.10 mmol, Example 1) in 600 mL of ethanol was saturated with hydrogen chloride gas for 20 minutes. The mixture was then refluxed for 12 hours, cooled, concentrated (to remove most of the ethanol), and partitioned between saturated sodium bicarbonate solution and chloroform (500 mL of each). Some solid would not dissolve into either phase. The mixture was filtered, giving 7.19 g (81%) of the title compound as a yellow solid, mp 258°-260° C., dec. The chloroform extract did contain more product, although not as clean.

Workup

  1. temperatureThe mixture was then refluxed for 12 hours
  2. temperaturecooled
  3. concentrationconcentrated (
  4. customto remove most of the ethanol), and
  5. custompartitioned between saturated sodium bicarbonate solution and chloroform (500 mL of each)
  6. dissolutionSome solid would not dissolve into either phase
  7. filtrationThe mixture was filtered

Sources & evidence

ORD record
ord-b5510ab619344d15bfe87d494208ec97
Source dataset
uspto-grants-1994_08
Patent number
US05342942

Reaction notes

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