Ammonia → 3-[2-(1,3-Dihydro-1,3-dioxo-2H-isoindol-2-yl) ethyl]-1H-indole-5-carbonitrile

HRID 1414024Notes

Reaction equation

HRID 1414024 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][CH2:12][N:13]1[C:21](=[O:22])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]1=[O:23].N.[CH3:25][N:26]1CCCC1=O>>[O:23]=[C:14]1[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:21](=[O:22])[N:13]1[CH2:12][CH2:11][C:5]1[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([C:25]#[N:26])[CH:3]=2)[NH:7][CH:6]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 13387N-methyl-2-pyrrolidoneHCID 19970994HCID 19970994, compound

Product 1

HCID 103809773-[2-(1,3-Dihydro-1,3-dioxo-2H-isoindol-2-yl) ethyl]-1H-indole-5-carbonitrile

Procedure

A mixture of 2-[2-(5-bromo-1H-indol-3-yl) ethyl]-1H-isoindole-1,3(2H)-dione (4.0 g), cuprous cyanide (1.1 g) and N-methyl-2-pyrrolidinone (10 ml) was heated at reflux for 1 hour. The reaction mixture was poured onto ice (30 g) and concentrated ammonia (15 ml) was added and the suspension was stirred for 0.75 hour. The solid was filtered off, washed with water and methanol and was crystallised from aqueous acetone to give the title compound (2.7 g) as a fawn solid m.p. 217°-221° C. T.L.C. Silica ether Rf 0.44.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 hour
  3. additionwas added
  4. filtrationThe solid was filtered off
  5. washwashed with water and methanol
  6. customwas crystallised from aqueous acetone

Sources & evidence

ORD record
ord-7074fd8eaa0d4316a46091417fc5fc2e
Source dataset
uspto-grants-1981_02
Patent number
US04252803

Reaction notes

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