Formic Acid → 1,2-Dihydro-6,7-dimethyl-2-oxo-3-quinolinecarbonitrile

HRID 2413149Notes

Reaction equation

HRID 2413149 reaction equation
Cl[C:2]1[C:11](C=O)=[CH:10][C:9]2[C:4](=[CH:5][C:6]([CH3:15])=[C:7]([CH3:14])[CH:8]=2)[N:3]=1.Cl.[NH2:17]O.[CH:19]([O-:21])=O.[Na+].C(O)=O>O>[C:2]([C:11]1[C:19](=[O:21])[NH:3][C:4]2[C:9]([CH:10]=1)=[CH:8][C:7]([CH3:14])=[C:6]([CH3:15])[CH:5]=2)#[N:17]

Participants

6

Reactant 4

HCID 284Formic AcidHCID 443297Hydroxyamine hydrochlorideHCID 7886572-Chloro-6,7-dimethylquinoline-3-carbaldehydeHCID 2723810Sodium Formate

Product 1

HCID 133714281,2-Dihydro-6,7-dimethyl-2-oxo-3-quinolinecarbonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture was prepared from 15 g of 2-chloro-6,7-dimethyl-3-quinolinecarboxaldehyde, 5.4 g of hydroxylamine hydrochloride, 8.5 g of sodium formate and 155 ml of 97% formic acid and this was heated at reflux for 3 hours. Initially, the mixture became a heavy yellow paste but a homogeneous brown solution formed later. However, by the end of the 3-hour reflux period, the mixture was again heterogeneous and it was cooled and poured into 300 ml of water. The solid which formed was separated by filtration and dried to give 3-cyano-6,7-dimethyl-2(1H)-quinolinone melting at about 300° C. The indicated product contained 1/4 molecule of water of hydration.

Workup

  1. temperaturethis was heated
  2. temperatureat reflux for 3 hours
  3. customa homogeneous brown solution formed later
  4. temperatureHowever, by the end of the 3-hour reflux period
  5. temperatureit was cooled
  6. customThe solid which formed
  7. customwas separated by filtration
  8. customdried

Sources & evidence

ORD record
ord-046707876d214298b02949f5aec9fa17
Source dataset
uspto-grants-1985_01
Patent number
US04496569

Reaction notes

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