N,O-Dimethylhydroxylamine → 5-Chloro-1-methyl-1H-indole-2-carboxylic acid methylamide

HRID 1362032Notes

Reaction equation

HRID 1362032 reaction equation
C([O:3][C:4]([C:6]1[N:7]([CH3:16])[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([Cl:15])=[CH:10][CH:9]=2)=O)C.CO[NH:19][CH3:20]>C1(C)C=CC=CC=1>[CH3:20][NH:19][C:4]([C:6]1[N:7]([CH3:16])[C:8]2[C:13]([CH:14]=1)=[CH:12][C:11]([Cl:15])=[CH:10][CH:9]=2)=[O:3]

Participants

4

Reactant 2

HCID 14232N,O-DimethylhydroxylamineHCID 3911003Ethyl 5-chloro-1-methyl-1H-indole-2-carboxylate

Product 1

HCID 594569125-Chloro-1-methyl-1H-indole-2-carboxylic acid methylamideYield 96%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a solution of 5-chloro-1-methyl-1H-indole-2-carboxylic acid ethyl ester (1.27 g, 5.3 mmol) in toluene (10 mL) was added O,N-dimethyl-hydroxylamine (9.6 mL of a 1 M solution in toluene, 9.6 mmol). The resulting mixture was heated to reflux overnight after which the reaction was cooled to room temperature and quenched by the addition of 10% aqueous K2CO3 (50 mL). The mixture was extracted with ethyl acetate (3×200 mL). The combined organic layers were washed with brine (100 mL), dried over Na2SO4, filtered and concentrated to give the title compound (2.12 g, 96%) as a yellow solid: 1H NMR (300 MHz, CDCl3) δ 7.59 (s, 1H), 7.27 (m, 2H), 6.73 (s, 1H), 6.13 (s, 1H), 4.03 (s, 3H), 3.01 (d, J=4.9 Hz, 3H); MS (ESI) m/e 222 (M+H)+.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux overnight after which the reaction
  3. customquenched by the addition of 10% aqueous K2CO3 (50 mL)
  4. extractionThe mixture was extracted with ethyl acetate (3×200 mL)
  5. washThe combined organic layers were washed with brine (100 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-d85a73380a764ab3931f1f4079309b61
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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