Hydrochloric Acid → HCID 63748402, compound

HRID 1944533Notes

Reaction equation

HRID 1944533 reaction equation
[OH-].[Na+].C[O:4][C:5]([C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[N:12]([CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH:11]=[CH:10]2)=[O:6].Cl>CO>[CH2:16]([N:12]1[C:13]2[C:9](=[CH:8][C:7]([C:5]([OH:6])=[O:4])=[CH:15][CH:14]=2)[CH:10]=[CH:11]1)[CH2:17][CH2:18][CH2:19][CH3:20]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 66815484HCID 66815484, compound

Product 1

HCID 63748402HCID 63748402, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Aqueous sodium hydroxide (1N, 3.4 mL, 3.4 mmol) was added to a solution of 1-pentyl-1H-indole-5-carboxylic acid methyl ester (0.79 g, 3.09 mmol) in methanol (30 mL). The resultant solution was heated at reflux for 4 hours. Additional aqueous sodium hydroxide (3.4 mL) was added and heating was continued for 4 hours. The solution was cooled, neutralized with 1N hydrochloric acid. The solvent was evaporated in vacuo. The residue was partitioned between water dichloromethane. The organic solution was dried over sodium sulfate and the solvent was evaporated in vacuo, to give the product, 0.715 g (100%). MS: m/z 232 (MH+). 1H NMR (CDCl3): 0.88 (t, 3 H), 1.24-1.42 (m, 4 H), 1.80-1.89 (m, 2 H), 4.14 (t, 2 H), 6.61 (d, 1 H), 7.16 (d, 1 H), 7.36 (d, 1 H), 7.99 (d of d, 1 H) and 8.50 (s, 1 H).

Workup

  1. temperatureat reflux for 4 hours
  2. temperatureheating
  3. temperatureThe solution was cooled
  4. customThe solvent was evaporated in vacuo
  5. customThe residue was partitioned between water dichloromethane
  6. dry with materialThe organic solution was dried over sodium sulfate
  7. customthe solvent was evaporated in vacuo
  8. customto give the product, 0.715 g (100%)

Sources & evidence

ORD record
ord-38d2d0431d25445dacd9e0ef8a306c7c
Source dataset
uspto-grants-2013_03
Patent number
US08394828B2

Reaction notes

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