Ammonia → 3-[(Dimethylamino)methyl]-2,3,4,9-tetrahydro-9-methyl-4-oxo-1H-carbazole-6-carboxamide

HRID 4385

Reaction equation

HRID 4385 reaction equation
[CH3:1][N:2]1[C:14]2[CH2:13][CH2:12][CH2:11][C:10](=[O:15])[C:9]=2[C:8]2[C:3]1=[CH:4][CH:5]=[C:6]([C:16]([NH2:18])=[O:17])[CH:7]=2.[CH2:19]=O.Cl.[CH3:22][NH:23][CH3:24].N>C(O)(=O)C>[CH3:22][N:23]([CH2:19][CH:11]1[C:10](=[O:15])[C:9]2[C:8]3[C:3](=[CH:4][CH:5]=[C:6]([C:16]([NH2:18])=[O:17])[CH:7]=3)[N:2]([CH3:1])[C:14]=2[CH2:13][CH2:12]1)[CH3:24]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 712FormaldehydeHCID 10473Dimethylamine, hydrochlorideHCID 201524492,3,4,9-Tetrahydro-9-methyl-4-oxo-1H-carbazole-6-carboxamide

Product 1

HCID 201524593-[(Dimethylamino)methyl]-2,3,4,9-tetrahydro-9-methyl-4-oxo-1H-carbazole-6-carboxamide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of the product of Stage (ii) (1.8 g), paraformaldehyde (0.3 g) and dimethylamine hydrochloride (0.75 g) in acetic acid (14 ml) was heated at 80°-100° under nitrogen for 2 h. The reaction mixture was cooled (20°), evaporated in vacuo and purified by flash chromatography (L) to give a foam. A sample (0.2 g) was stirred in 0.88 ammonia 10 ml) for 3 days to precipitate to title compound (100 mg) as a solid. m.p. 171°-173° (foams).

Workup

  1. temperaturewas heated at 80°-100° under nitrogen for 2 h
  2. temperatureThe reaction mixture was cooled (20°)
  3. customevaporated in vacuo
  4. custompurified by flash chromatography (L)
  5. customto give a foam
  6. customto precipitate to title compound (100 mg) as a solid

Sources & evidence

ORD record
ord-45ebea4005c547ca92a07b1f8fb6a84c
Source dataset
uspto-grants-1988_02
Patent number
US04725615

Linked notes

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