Hydrochloric Acid → HCID 6603242, compound

HRID 1379760Notes

Reaction equation

HRID 1379760 reaction equation
[ClH:1].[CH3:2][C:3]1[CH:10]=[CH:9][C:8]([CH3:11])=[C:5]([C:6]#[N:7])[C:4]=1[NH2:12].[CH3:13][C:14]1([CH3:22])[CH2:21][C:19](=O)[CH2:18][C:16](=[O:17])[CH2:15]1>C1COCC1>[ClH:1].[CH3:13][C:14]1([CH3:22])[CH2:21][C:19]([NH:12][C:4]2[C:3]([CH3:2])=[CH:10][CH:9]=[C:8]([CH3:11])[C:5]=2[C:6]#[N:7])=[CH:18][C:16](=[O:17])[CH2:15]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 31358DimedoneHCID 22908082HCID 22908082, compound

Product 1

HCID 6603242HCID 6603242, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6 ml of concentrated hydrochloric acid were added to a solution of 5.84 g (0.04 mol) of 3,6-dimethylanthranilonitrile (Ib) in 80 ml of THF with stirring, after 15 min 5.6 g (0.04 mol) of dimedone (II) were added, the mixture was heated under reflux with stirring for 14 h, the precipitate was filtered off, washed with acetone and dried. The mother liquor was concentrated to 1/4 of the initial volume, the precipitate was filtered off, washed with acetone and dried. Precipitates were combined to give 10.5 g (87%) of IIId, m.p. 208-209 (i-PrOH).

Workup

  1. additionwere added
  2. temperaturethe mixture was heated
  3. temperatureunder reflux
  4. filtrationthe precipitate was filtered off
  5. washwashed with acetone
  6. customdried
  7. concentrationThe mother liquor was concentrated to 1/4 of the initial volume
  8. filtrationthe precipitate was filtered off
  9. washwashed with acetone
  10. customdried
  11. customPrecipitates
  12. customto give 10.5 g (87%) of IIId, m.p. 208-209 (i-PrOH)

Sources & evidence

ORD record
ord-5c0274006f6342b6850e67287ebf61fb
Source dataset
uspto-grants-1997_09
Patent number
US05672707

Reaction notes

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