3-Azido-4-phenylcarbostyril → 5,7-Dihydro-6H-indolo[2,3-c]quinolin-6-one

HRID 597559Notes

Reaction equation

HRID 597559 reaction equation
[N:1]([C:4]1[C:5](=[O:20])[NH:6][C:7]2[C:12]([C:13]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N+]=[N-]>C1(C)C=CC=CC=1>[CH:11]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:12]=1[C:13]1[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[NH:1][C:4]=1[C:5](=[O:20])[NH:6]2

Participants

3

Reactant 1

HCID 214454403-Azido-4-phenylcarbostyril

Product 1

HCID 214454105,7-Dihydro-6H-indolo[2,3-c]quinolin-6-one

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A suspension of 114 g. of 3-azido-4-phenylcarbostyril in 2 l. of toluene was heated to reflux until nitrogen evolution ceased (5 hours). On cooling, 7H-indolo[2,3-c]quinolin-6(5H)-one crystallized; 84.7 g. (84 percent), having a melting point of 314°-316° .

Workup

  1. additionA suspension of 114 g
  2. temperatureto reflux until nitrogen evolution
  3. custom(5 hours)
  4. temperatureOn cooling
  5. custom7H-indolo[2,3-c]quinolin-6(5H)-one crystallized

Sources & evidence

ORD record
ord-5d91ec22b5fb4b4598e6fe69f48e7afd
Source dataset
uspto-grants-1977_03
Patent number
US04014883

Reaction notes

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