Isopropanol → HCID 178459484, compound

HRID 428427Notes

Reaction equation

HRID 428427 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-f09f6840a9a2425b820a8476986ec3bd
Source dataset
uspto-grants-2001_11
Patent number
US06313290B1

Reaction notes

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