(4-Methylphenyl)hydrazine → HCID 21220552, compound

HRID 1584723Notes

Reaction equation

HRID 1584723 reaction equation
Br.O=[C:3]1[CH:12]([CH2:13][C:14]([O:16]C)=O)[CH2:11][CH2:10][C:9]2[CH:8]=[N:7][CH:6]=[CH:5][C:4]1=2.[C:18]1([CH3:26])[CH:23]=[CH:22][C:21]([NH:24][NH2:25])=[CH:20][CH:19]=1.Cl.C1(C)C=CC(NN)=CC=1>C1(C)C(C)=CC=CC=1>[CH3:26][C:18]1[CH:23]=[CH:22][C:21]([N:24]2[C:14](=[O:16])[CH2:13][CH:12]3[C:3]([C:4]4[CH:5]=[CH:6][N:7]=[CH:8][C:9]=4[CH2:10][CH2:11]3)=[N:25]2)=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 10875(4-Methylphenyl)hydrazineHCID 125044-Methylphenylhydrazine monohydrochlorideHCID 70281472HCID 70281472, compound

Product 1

HCID 21220552HCID 21220552, compoundYield 25.8%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

Methyl 5,6,7,8-tetrahydro-5-oxoisoquinoline-6-acetate hydrobromide (1.2 g) (Wu et al, Synthetic Communications 24, 273 (1994)) 4-tolylhydrazine (0.5 g) and 4-tolylhydrazine hydrochloride (0.19 g) in xylene (20 ml) were heated under reflux for 3 hours. The reaction mixture was allowed to cool to room temperature and the volatiles removed. The residue was dissolved in dichloromethane-methanol, washed with sodium hydrogen carbonate solution twice and then brine. The organic phase was dried, filtered and concentrated to a dark oil. The crude product was adsorbed onto silica and chromatographed eluting with 7:3 dichloromethane:ethyl acetate. The resultant oil was triturated with ether and recrystallised from isopropanol to give the title compound (0.3 g).

Workup

  1. temperatureunder reflux for 3 hours
  2. customthe volatiles removed
  3. dissolutionThe residue was dissolved in dichloromethane-methanol
  4. washwashed with sodium hydrogen carbonate solution twice
  5. customThe organic phase was dried
  6. filtrationfiltered
  7. concentrationconcentrated to a dark oil
  8. customchromatographed
  9. washeluting with 7:3 dichloromethane
  10. customThe resultant oil was triturated with ether
  11. customrecrystallised from isopropanol

Sources & evidence

ORD record
ord-a4839844fda0447fb58653e21cb4eae3
Source dataset
uspto-grants-1999_08
Patent number
US05935956

Reaction notes

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