Hydrochloric Acid → 5-methyl-1-oxo-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]indole-8-carboxylic acid

HRID 1748271Notes

Reaction equation

HRID 1748271 reaction equation
[OH-].[Na+].[CH3:3][CH:4]1[N:10]2[C:11]3[CH:12]=[C:13]([C:18]([O:20]CC)=[O:19])[CH:14]=[CH:15][C:16]=3[CH:17]=[C:9]2[C:8](=[O:23])[NH:7][CH2:6][CH2:5]1.Cl>C(O)C>[CH3:3][CH:4]1[N:10]2[C:11]3[CH:12]=[C:13]([C:18]([OH:20])=[O:19])[CH:14]=[CH:15][C:16]=3[CH:17]=[C:9]2[C:8](=[O:23])[NH:7][CH2:6][CH2:5]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67235486ethyl 5-methyl-1-oxo-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]indole-8-carboxylate

Product 1

HCID 672353965-methyl-1-oxo-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]indole-8-carboxylic acidYield 93.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

1 NaOH solution (60 mL, 60 mmol) is added to a solution of ethyl 5-methyl-1-oxo-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-a]indole-8-carboxylate (7.0 g, 24 mmol) in ethanol (75 mL). The reaction mixture is refluxed for 1.5 h. Then the reaction mixture is acidified with 1M HCl and ethanol is removed under vacuum. The resulting solid is filtered, washed with water and dried to afford the title compound (5.8 g, 92%) as a solid.

Workup

  1. temperatureThe reaction mixture is refluxed for 1.5 h
  2. customis removed under vacuum
  3. filtrationThe resulting solid is filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-b4099f8b93fd4d88b2fd38f6f876c00e
Source dataset
uspto-grants-2015_10
Patent number
US09150577B2

Reaction notes

Loading…