Water → 3-(Cyclohex-1-en-1-yl)-1H-indole-6-carboxylic acid

HRID 1713920Notes

Reaction equation

HRID 1713920 reaction equation
C[O:2][C:3]([C:5]1[CH:13]=[C:12]2[C:8]([CH:9]=[CH:10][NH:11]2)=[CH:7][CH:6]=1)=[O:4].[C:14]1(=O)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.C[O-].[Na+].O>CO>[C:14]1([C:9]2[C:8]3[C:12](=[CH:13][C:5]([C:3]([OH:2])=[O:4])=[CH:6][CH:7]=3)[NH:11][CH:10]=2)[CH2:19][CH2:18][CH2:17][CH2:16][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7967CyclohexanoneHCID 639844Methyl indole-6-carboxylateHCID 10942334Sodium Methoxide

Product 1

HCID 111840773-(Cyclohex-1-en-1-yl)-1H-indole-6-carboxylic acidYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of methyl-indole-6-carboxylate in MeOH (1.7 M) was added cyclohexanone (3.0 eq.) followed by 30% NaOMe in MeOH (6.0 eq.) in 100 ml portions over 20 min. The resulting mixture was stirred at RT for 45 min and refluxed for 8 h. Water was added, and the mixture stirred at RT until all solids had dissolved. The organic solvent was removed under vacuum and the pH of the aqueous phase adjusted to 1, by slow addition of concentrated HCl at 0° C. The precipitate was isolated by filtration, and then washed with water, until the pH of the water reached 6-7. Drying under high, vacuum gave the title compound as a beige solid (100%). 1H NMR (300 MHz, DMSO-d6, 300 K) δ 1.49-1.98 (m, 8H), 6.22 (bs, 1H), 7.50 (s, 1H), 7.64 (d, J 7.6, 1H), 7.75 (d, J 7.6, 1H), 8.02 (s, 1H), 11.39 (s, 1H); MS (ES+) m/z 242 (M+H)+.

Workup

  1. temperaturerefluxed for 8 h
  2. stirringthe mixture stirred at RT until all solids
  3. dissolutionhad dissolved
  4. customThe organic solvent was removed under vacuum
  5. additionthe pH of the aqueous phase adjusted to 1, by slow addition of concentrated HCl at 0° C
  6. customThe precipitate was isolated by filtration
  7. washwashed with water, until the pH of the water
  8. customDrying under high, vacuum

Sources & evidence

ORD record
ord-c0216ed528524b9d91a1f30cac664f7b
Source dataset
uspto-grants-2010_09
Patent number
US07795250B2

Reaction notes

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