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 626870Notes

Reaction equation

HRID 626870 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-e9fb28d5f15548ff98ae9ac24c8c7b16
Source dataset
uspto-grants-2016_04
Patent number
US09309253B2

Reaction notes

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