Sodium Hydroxide → HCID 21930949, compound

HRID 75251Notes

Reaction equation

HRID 75251 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-3a728c7fc1e14f44ad2c063ed23ea009
Source dataset
uspto-grants-2014_09
Patent number
US08835424B2

Reaction notes

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