N-methyl-2-pyrrolidone → HCID 19592796, compound

HRID 613569Notes

Reaction equation

HRID 613569 reaction equation
Cl[C:2]1[C:11]2[C:6](=[C:7]([NH:13][C:14](=O)[C:15]3[C:20]([Cl:21])=[CH:19][CH:18]=[CH:17][C:16]=3[Cl:22])[CH:8]=[C:9]([CH3:12])[CH:10]=2)[N:5]=[CH:4][CH:3]=1.[OH2:24].[NH2:25][NH2:26].CN1C[CH2:31][CH2:30][C:29]1=O>C(OCC)(=O)C>[Cl:22][C:16]1[CH:17]=[CH:18][CH:19]=[C:20]([Cl:21])[C:15]=1[C:14]([NH:13][C:7]1[CH:8]=[C:9]([CH3:12])[CH:10]=[C:11]2[C:6]=1[N:5]=[CH:4][CH:3]=[C:2]2[NH:25][N:26]=[C:30]([CH3:31])[CH3:29])=[O:24]

Participants

5

Reactant 3

HCID 13387N-methyl-2-pyrrolidoneHCID 24654Hydrazine hydrate (1:1)HCID 19592532HCID 19592532, compound

Product 1

HCID 19592796HCID 19592796, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 4-chloro-8-(2,6-dichlorobenzoylamino)-6-methylquinoline (562 mg) in N-methylpyrrolidone (6 ml) was added hydrazine hydrate, and the mixture was heated at 90° C. for 6 hours. The mixture was diluted with ethyl acetate, washed with water and brine, dried over magnesium sulfate and concentrated. The residue was dissolved in methylene chloride and acetone and then concentrated. The residual solid was treated with hot ethanol (5 ml), allowed to cool to ambient temperature, filtered and washed with ethanol to give 8-(2,6-dichlorobenzoylamino)-6-methyl-4-(2-isopropylidenehydrazino)quinoline (560 mg) as an off-white crystal.

Workup

  1. washwashed with water and brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in methylene chloride
  5. concentrationacetone and then concentrated
  6. additionThe residual solid was treated with hot ethanol (5 ml)
  7. temperatureto cool to ambient temperature
  8. filtrationfiltered
  9. washwashed with ethanol

Sources & evidence

ORD record
ord-254301213dec4edaaf2716d29c6cd56c
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

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