Sulfuric Acid → 2,3,4,9-Tetrahydro-9-methyl-4-oxo-1H-carbazole-6-carboxamide

HRID 4384

Reaction equation

HRID 4384 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]#[N:17])[CH:7]=2.S(=O)(=O)(O)[OH:19]>>[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]([NH2:17])=[O:19])[CH:7]=2

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 201524412,3,4,9-Tetrahydro-9-methyl-4-oxo-1H-carbazole-6-carbonitrile

Product 1

HCID 201524492,3,4,9-Tetrahydro-9-methyl-4-oxo-1H-carbazole-6-carboxamide

Procedure

A solution of the product of Stage (i) cyanonitrile (2.7 g) in concentrated sulphuric acid (30 ml) was heated at 80° for 1 h. The mixture was poured onto ice (ca. 500 g) to precipitate a solid which was filtered, washed with water (3×50 ml) and dried in vacuo to leave a solid (3.1 g). This was extracted with boiling absolute ethanol (1.5 l), the extract was evaporated to ca 2 ml, diluted with a mixture of chloroform:methanol (1:1, ca 20 ml) and filtered to give the title compound (0.53 g) as a solid m.p. 295°-298°.

Workup

  1. additionThe mixture was poured onto ice (ca. 500 g)
  2. customto precipitate a solid which
  3. filtrationwas filtered
  4. washwashed with water (3×50 ml)
  5. customdried in vacuo

Sources & evidence

ORD record
ord-c419ae0f44f44e4fa86eadeb58039dce
Source dataset
uspto-grants-1988_02
Patent number
US04725615

Linked notes

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