Sodium Hydroxide → HCID 21930949, compound

HRID 1768331Notes

Reaction equation

HRID 1768331 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[CH:12]=[N:13][C:14]([C:15]([O:17]CC)=[O:16])=[C:10]3[CH2:9][N:8]=[C:7]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:6]=2[CH:26]=1.[OH-].[Na+]>CCO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[CH:12]=[N:13][C:14]([C:15]([OH:17])=[O:16])=[C:10]3[CH2:9][N:8]=[C:7]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:6]=2[CH:26]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 21930956Ethyl 8-bromo-6-phenyl-4H-benzo[f]imidazo[1,5-a][1,4]diazepine-3-carboxylate

Product 1

HCID 21930949HCID 21930949, compoundYield 96.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The ester 5 (2 g) was dissolved in EtOH (50 mL) and aq sodium hydroxide (10 mL, 2N) was added to the solution. The mixture was heated to reflux for half an hour. After the EtOH was removed under reduced pressure, the solution was allowed to cool. The pH value was adjusted to 4 by adding 10% aq HCl dropwise. The mixture was filtered and the solid was washed with water and ethyl ether. The solid was dried to provide 27 (1.8 g, 96.6%): mp>250° C.; IR (KBr) 3450 (b), 2844, 1707, 1615, 1493, 1166, 700 cm−1; 1H NMR (300 MHz, DMSO-d6) δ 4.14 (d, 1H, J=12.6 Hz), 5.79 (d, 1H, 12.6 Hz), 7.41-7.54 (m, 6H), 7.88 (d, 1H, J=8.7 Hz), 8.03 (dd, 1H, J=8.7 Hz, J=2.1 Hz), 8.47 (s, 1H); MS (EI) m/e (rel intensity) 381 (M+, 20), 383 (19).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for half an hour
  3. customAfter the EtOH was removed under reduced pressure
  4. temperatureto cool
  5. additionby adding 10% aq HCl dropwise
  6. filtrationThe mixture was filtered
  7. washthe solid was washed with water and ethyl ether
  8. customThe solid was dried

Sources & evidence

ORD record
ord-d8215e37de774a7f98585974a952745b
Source dataset
uspto-grants-2007_06
Patent number
US07235656B2

Reaction notes

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