Hydrogen Bromide → HCID 135600005, compound

HRID 1175802Notes

Reaction equation

HRID 1175802 reaction equation
[NH2:1][C:2]1[N:3]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:4]=[C:5]2[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[N:8](CC3C=CC=CC=3)[C:7](=[O:22])[C:6]=12.Br.[OH-].[Na+]>C(O)(=O)C>[NH2:1][C:2]1[N:3]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[N:4]=[C:5]2[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[NH:8][C:7](=[O:22])[C:6]=12

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 14798Sodium HydroxideHCID 23153933HCID 23153933, compound

Product 1

HCID 135600005HCID 135600005, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 3-amino-5-benzyl-2-phenyl-2,5-dihydro-4H-pyrazolo[4,3-c]quinolin-4-one (0.26 g), 48% aqueous hydrobromic acid (8 ml) and acetic acid (1.3 ml) was heated at 100° C. for 36 hours. After cooling, ice was added thereto, and basified by adding an 11N aqueous sodium hydroxide solution. The precipitated crystal was collected by filtration, washed with water and dried. Methanol and ethyl acetate were added to the crystal, and the mixture was heated under reflux for 10 minutes. After cooling, the precipitated crystal was collected by filtration to obtain the target compound (47 mg).

Workup

  1. temperatureAfter cooling
  2. additionice was added
  3. filtrationThe precipitated crystal was collected by filtration
  4. washwashed with water
  5. customdried
  6. additionMethanol and ethyl acetate were added to the crystal
  7. temperaturethe mixture was heated
  8. temperatureunder reflux for 10 minutes
  9. temperatureAfter cooling
  10. filtrationthe precipitated crystal was collected by filtration

Sources & evidence

ORD record
ord-103b94e4327c4eb2a624f8d9f9451b6f
Source dataset
uspto-grants-2010_11
Patent number
US07842701B2

Reaction notes

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