N,N,N',N',N'',N''-Hexamethylmethanetriamine → Methyl (6E)-6-[(dimethylamino)methylidene]-1-methyl-7-oxo-4,5,6,7-tetrahydro-1H-indole-3-carboxylate

HRID 872192Notes

Reaction equation

HRID 872192 reaction equation
[CH3:1][N:2]1[C:10]2[C:9](=[O:11])[CH2:8][CH2:7][CH2:6][C:5]=2[C:4]([C:12]([O:14][CH3:15])=[O:13])=[CH:3]1.[CH3:16][N:17]([CH:19](N(C)C)N(C)C)[CH3:18]>>[CH3:16][N:17](/[CH:19]=[C:8]1\[CH2:7][CH2:6][C:5]2[C:4]([C:12]([O:14][CH3:15])=[O:13])=[CH:3][N:2]([CH3:1])[C:10]=2[C:9]\1=[O:11])[CH3:18]

Participants

3

Reactant 2

HCID 79831N,N,N',N',N'',N''-HexamethylmethanetriamineHCID 68276330Methyl 1-methyl-7-oxo-4,5,6,7-tetrahydro-1H-indole-3-carboxylate

Product 1

HCID 68356011Methyl (6E)-6-[(dimethylamino)methylidene]-1-methyl-7-oxo-4,5,6,7-tetrahydro-1H-indole-3-carboxylate

Conditions

Temperature
90 °C

Procedure

Methyl 1-methyl-7-oxo-4,5,6,7-tetrahydro-1H-indole-3-carboxylate (288 mg, 1.39 mmol) was treated with tris(dimethylamino)methane (2.4 mL, 13.9 mmol) and the reaction mixture was stirred at 90° C. for 10 h. Volatiles were removed under reduced pressure and the residue used without further purification.

Workup

  1. customVolatiles were removed under reduced pressure
  2. customthe residue used without further purification

Sources & evidence

ORD record
ord-e670ee0f110645728dfb80702b675954
Source dataset
uspto-grants-2015_03
Patent number
US08975267B2

Reaction notes

Loading…