Sodium Hydroxide → HCID 67086290, compound

HRID 1511961Notes

Reaction equation

HRID 1511961 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:5])[CH3:2].[Cl-].[NH4+:16].[OH-].[Na+].[OH-].[NH4+].[O-]Cl.[Na+]>CC(OC)(C)C.CCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)C.[Cl-].CCOC(C)=O>[CH2:1]([O:3][C:4]([C:6]1[N:7]([NH2:16])[C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:5])[CH3:2]

Participants

9

Reactant 5

HCID 14798Sodium HydroxideHCID 14923Ammonium HydroxideHCID 25517Ammonium ChlorideHCID 73125Ethyl indole-2-carboxylateHCID 23665760Sodium Hypochlorite2×

Product 1

HCID 67086290HCID 67086290, compoundYield 66.2%

Reagents, catalysts & solvents 3

HCID 21218Trioctylmethylammonium chlorideCatalystHCID 8857Ethyl AcetateSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

To a mixture of 1H-indole-2-carboxylic acid ethyl ester (2.07 g, Sigma-Aldridch) in MTBE (25 mL) was added in the order of: ammonium chloride (2.96 g), ALIQUAT 336 (124 mg; Cognis Corp., Monheim, Germany), sodium hydroxide (7.44 g), concentrated ammonium hydroxide solution (4.06 mL); the resulting mixture was rigorously stirred at rt, then a 10% solution of NaOCl (67 mL) was added dropwise over a period of 30 min. The reaction was stirred for 3 h after addition of NaOCl, then diluted with EtOAc, washed with water and sat. NaCl solution respectively, dried over sodium sulfate, filtered, concentrated, then the residue was column-purified to give product (1.48 g) as slightly yellow oil. 1H NMR (CDCl3, δ in ppm): 7.65-7.58 (m, 2H), 7.35 (t, 1H, J=7.0 Hz), 7.18-7.11 (m, 2H), 6-4.5 (very broad, 2H), 4.38 (q, 2H, J=7.0 Hz), 1.42 (t, 3H, J=7.0 Hz).

Workup

  1. stirringThe reaction was stirred for 3 h
  2. washwashed with water and sat. NaCl solution respectively
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customthe residue was column-purified

Sources & evidence

ORD record
ord-b01ad798ed8248b0b81fee38e74da6bd
Source dataset
uspto-grants-2012_07
Patent number
US08217043B2

Reaction notes

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