Isopropanol → HCID 178459484, compound

HRID 1954742Notes

Reaction equation

HRID 1954742 reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][C:5]2[C:6](=[O:20])[C:7]3[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[N:13][NH:12][C:8]=3[C:9](=[O:11])[NH:10][C:4]=2[CH:3]=1.[CH3:23]C(O)C>Cl>[Cl:1][C:2]1[CH:22]=[CH:21][C:5]2[C:6](=[O:20])[C:7]3[C:14]([C:15]([O:17][CH:18]([CH3:23])[CH3:19])=[O:16])=[N:13][NH:12][C:8]=3[C:9](=[O:11])[NH:10][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 3776IsopropanolHCID 1784704817-Chloro-3-(ethoxycarbonyl)pyrazolo[3,4-c][1]benzazepine-4,10-(1H,9H)dione

Product 1

HCID 178459484HCID 178459484, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidCatalyst

Procedure

A solution of 7-chloro-3-(ethoxycarbonyl)pyrazolo[3,4-c][1]benzazepine-4,10(1H,9H)-dione (500 mg, 1.56 mmol), 2-propanol (60 mL), and concentrated hydrochloric acid (3 drops) was subjected to three cycles of partial solvent removal by slow distillation (over 6 hours) followed by overnight reflux. After the third cycle, solvent was removed by rotary evaporation and the crude product was purified by flash chromatography eluting with dichloromethane:2-propanol (95:5-85:15) to yield the title compound as a white solid (256 mg, 48%, m.p. 291° C). Alternatively, the title compound can be prepared as described in Example 18 shown hereinbelow in Table 1.

Workup

  1. temperaturereflux
  2. customAfter the third cycle, solvent was removed by rotary evaporation
  3. customthe crude product was purified by flash chromatography
  4. washeluting with dichloromethane:2-propanol (95:5-85:15)

Sources & evidence

ORD record
ord-0bea96bc1f4340cb9dd29795c317afc6
Source dataset
uspto-grants-2000_09
Patent number
US06124281

Reaction notes

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