Methyl carbazate → HCID 68469477, compound

HRID 507374Notes

Reaction equation

HRID 507374 reaction equation
[CH3:1][O:2][C:3]([NH:5][NH2:6])=[O:4].[CH3:7][N:8]([CH3:22])[CH2:9][CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([CH:20]=O)[CH:18]=2)[NH:13][CH:12]=1>CO>[CH3:1][O:2][C:3]([NH:5][N:6]=[CH:20][C:17]1[CH:18]=[C:19]2[C:14](=[CH:15][CH:16]=1)[NH:13][CH:12]=[C:11]2[CH2:10][CH2:9][N:8]([CH3:22])[CH3:7])=[O:4]

Participants

4

Reactant 2

HCID 80519Methyl carbazateHCID 99908943-(2-dimethylamino-ethyl)-1H-indole-5-carbaldehyde

Product 1

HCID 68469477HCID 68469477, compoundYield 104%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of hydrazinecarboxylic acid methyl ester (0.90 g, 10 mmol) in methanol (10 ml) is added 3-(2-Dimethylamino-ethyl)-1H-indole-5-carbaldehyde (2.16 g, 10 mmol), and the mixture obtained is heated at reflux for 20 hours. After removal of the solvent, a yellow oil (3.0 g) is obtained, which is chromatographed on silica (chloroform:methanol 9:1 v:v to 4:1 v:v) to give 1.6 g (55.4%) of the product as a colourless foam. 1H-NMR (CDCl3, 300 MHz) δ 2.26 (s, 6H, N(CH3)2); 2.57, 2.84 (2 m, 2H each, CH2CH2NHMe2); 3.79 (s, 3H, OCH3); 6.90 (s, 1H, H-2); 7.11 (d, 1H, J=8.5 Hz, H-7); 7.45 (dd, 1H, J=1.5 Hz, H-6); 7.62 (br s, 1H, H-4); 7.77 (s, 1H, N═CH); 9.04 (br s, 1H, H-1); 9.33 (br s, 1H, NH). 13C-NMR (CDCl3, 75 MHz) δ 23.73 (CH2); 45.51 (N(CH3)2); 53.04 (OCH3); 60.39 (CH2NMe2); 112.07 (C-7); 114.66 (C-3); 119.52 (C-4); 120.72 (C-6); 123.14 (C-2); 125.14 (C-5); 127.52 (C-9); 137.71 (C-8); 147.25 (N═CH); 155.02 (NC═O).

Workup

  1. customthe mixture obtained
  2. temperatureis heated
  3. temperatureat reflux for 20 hours
  4. customAfter removal of the solvent

Sources & evidence

ORD record
ord-0f7c61e69bf64758bc80434e74a2fb0c
Source dataset
uspto-grants-2010_08
Patent number
US07786156B2

Reaction notes

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