Methanol → 6-oxo-3,4,5,6-tetrahydro-1H-azepino[5,4,3-cd]indole-2-carboxylic acid

HRID 33331Notes

Reaction equation

HRID 33331 reaction equation
C([O:9][C:10]([C:12]1[NH:13][C:14]2[CH:15]=[CH:16][CH:17]=[C:18]3[C:24](=[O:25])[NH:23][CH2:22][CH2:21][C:20]=1[C:19]=23)=[O:11])CCCCCCC.[OH-].[Li+].CO>O>[O:25]=[C:24]1[C:18]2[C:19]3[C:20](=[C:12]([C:10]([OH:11])=[O:9])[NH:13][C:14]=3[CH:15]=[CH:16][CH:17]=2)[CH2:21][CH2:22][NH:23]1

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 183399926-oxo-3,4,5,6-tetrahydro-1H-azepino[5,4,3-cd]indole-2-carboxylic acid octyl ester

Product 1

HCID 111281096-oxo-3,4,5,6-tetrahydro-1H-azepino[5,4,3-cd]indole-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

6-Oxo-3,4,5,6-tetrahydro-1H-azepino[5,4,3-cd]indole-2-carboxylic acid octyl ester (Example FFF) (350 mg, 1.02 mmol) and lithium hydroxide (122 mg, 5.11 mmol) were dissolved in 10 mL 2:1 methanol:water and stirred at room temperature for 24 h. The reaction mixture was diluted with water then washed twice with dichloromethane. The aqueous solution was acidified to ca. pH 2 with conc. HCl. The white precipitate was collected by filtration, washed with water, and dried in vacuo to yield 6-oxo-3,4,5,6-tetrahydro-1H-azepino[5,4,3-cd]indole-2-carboxylic acid, 235 mg (99%) as a white solid: m.p. 298-299° C. (dec); 1H NMR (300 MHz, d6-DMSO) δ 3.17 (m, 2H), 3.41 (m, 2H), 7.35 (t, J=7.8 Hz, 1H), 7.59 (d, J=8.1 Hz, 1H), 7.73 (d, J=7.5 Hz, 1H), 8.14 (br t, 1H), 11.77 (br s, 1H), 13.14 (br s, 1H). MS (electrospray, MH+): 231. Anal. (C12H10N2O3.1.0 H2O) C, H, N.

Workup

  1. washthen washed twice with dichloromethane
  2. filtrationThe white precipitate was collected by filtration
  3. washwashed with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-9cc592a330264dfaa537f8766d9f1c19
Source dataset
uspto-grants-2008_09
Patent number
US07429578B2

Reaction notes

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