(3-Chlorophenyl)hydrazine → 7-Chloro-2,5-dihydro-1H-pyrido[4,3-b]indol-1-one

HRID 1970990Notes

Reaction equation

HRID 1970990 reaction equation
[OH:1][C:2]1[CH:7]=[C:6](O)[CH:5]=[CH:4][N:3]=1.[Cl:9][C:10]1[CH:11]=[C:12]([NH:16]N)[CH:13]=[CH:14][CH:15]=1>C1(OC2C=CC=CC=2)C=CC=CC=1.C1(C)C=CC=CC=1>[Cl:9][C:10]1[CH:15]=[CH:14][C:13]2[C:7]3[C:2](=[O:1])[NH:3][CH:4]=[CH:5][C:6]=3[NH:16][C:12]=2[CH:11]=1

Participants

5

Reactant 2

HCID 75332(3-Chlorophenyl)hydrazineHCID 178516518HCID 178516518, compound

Product 1

HCID 565951877-Chloro-2,5-dihydro-1H-pyrido[4,3-b]indol-1-one

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 7583Diphenyl EtherSolvent

Conditions

Temperature
175 °C

Procedure

To 2,4-dihydroxypyridine (25.0 g, 225 mmol) in phenyl ether (400 mL) in a three neck flask fitted with a Dean-Stark trap was added 3-chlorophenylhydrazine. The reaction mixture was heated to 175° C. for 1 h, and to 230° C. for 3 h. The reaction mixture was allowed to cool to room temperature and diluted with toluene. The mixture was filtered, washed with MeOH, and dried. The collected solids were ground to fine power, slurried in MeOH, and sonicated for 5 min. The slurry was filtered, washed with MeOH, and dried to give the title compound. 1H NMR (600 MHz, CD3SOCD3) δ 11.83 (s, 1H); 11.19 (s, 1H); 8.05 (d, 1H); 7.53 (d, 1H); 7.32 (t, 1H); 7.21 (dd, 1H); 6.52 (d, 1H). LRMS (APCI) calc'd for (C11H7ClN2O) [M+H]+, 219.0. found 219.1.

Workup

  1. temperatureto cool to room temperature
  2. filtrationThe mixture was filtered
  3. washwashed with MeOH
  4. customdried
  5. customsonicated for 5 min
  6. filtrationThe slurry was filtered
  7. washwashed with MeOH
  8. customdried

Sources & evidence

ORD record
ord-802c9cee994c41fb9211700000513433
Source dataset
uspto-grants-2013_04
Patent number
US08431569B2

Reaction notes

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