Water → HCID 21107343, compound

HRID 1361026Notes

Reaction equation

HRID 1361026 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[NH:6][C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][CH:10]=[CH:9][CH:8]=3.O.[CH3:16][N:17]1CCCC1=O>>[C:16]([C:2]1[CH:3]=[CH:4][C:5]2[NH:6][C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][CH:10]=[CH:9][CH:8]=3)#[N:17]

Participants

4

Reactant 3

HCID 962WaterHCID 13387N-methyl-2-pyrrolidoneHCID 2524463-Bromocarbazole

Product 1

HCID 21107343HCID 21107343, compoundYield 40%

Procedure

A solution of 3-bromo-9H-carbazole (23.08 g, 0.094 mol) and cuprous cyanide (9.33 g, 0.103 mol) in N-methyl-pyrrolidone (300 ml) was heated at 200° C. for 5 h. The cooled reaction mixture was poured on to water (600 ml) and the precipitate was filtered off and washed with ethyl acetate (3×50 ml). The filtrate was extracted with ethyl acetate (3×250 ml) and the combined ethyl acetate extracts were washed with water (150 ml), brine (150 ml), dried (MgSO4) and concentrated in vacuo. The residue was crystallised from heptanes and recrystallised from acetonitrile (70 ml) affording 7.16 g (40%) of 3-cyano-9H-carbazole as a solid.

Workup

  1. customThe cooled reaction mixture
  2. filtrationthe precipitate was filtered off
  3. washwashed with ethyl acetate (3×50 ml)
  4. extractionThe filtrate was extracted with ethyl acetate (3×250 ml)
  5. washthe combined ethyl acetate extracts were washed with water (150 ml), brine (150 ml)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customThe residue was crystallised from heptanes
  9. customrecrystallised from acetonitrile (70 ml)

Sources & evidence

ORD record
ord-602db85a9d484ddda6a95503d9b1705f
Source dataset
uspto-grants-2011_02
Patent number
US07879893B2

Reaction notes

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