Acetic Acid → HCID 14853005, compound

HRID 845065Notes

Reaction equation

HRID 845065 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=O)[C:8]([CH2:15][C:16]([OH:18])=O)([CH3:14])[CH2:7][CH2:6]2)#[N:2].O.[NH2:20][NH2:21].C(O)(=O)C>O>[C:1]([C:3]1[CH:12]=[CH:11][C:10]2[C:9]3[C:8]([CH3:14])([CH2:15][C:16](=[O:18])[NH:20][N:21]=3)[CH2:7][CH2:6][C:5]=2[CH:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 24654Hydrazine hydrate (1:1)HCID 14853004HCID 14853004, compound

Product 1

HCID 14853005HCID 14853005, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 6-cyano-2-methyl-1-oxo-1,2,3,4-tetrahydro-2-naphthyl acetic acid (3.5 g), hydrazine hydrate (20 ml), acetic acid (20 ml) and water (40 ml) was stirred under reflux for 4 hours. The reaction mixture was cooled and the precipitated solid filtered off. Recrystallisation from DMF/ethanol gave 8-cyano-4a-methyl-4,4a,5,6-tetrahydrobenzo[h]cinnolin-3[2H]-one (2.5 g; m.p.>300°); ν(Nujol mull) 3315, 3210, 2214, 1675, 1635, 1615, 1590 and 844 cm-1 ; δ(DMSO-d6) 1.06, (3H,s,CH3), 1.80 (2H,m,5-H) 2.40 (2H,m,4-H), 2.92 (2H,m,6-H), 7.61 (1H,m,9-H), 7.70 (1H, s, 7-H), 8.13 (1H,d,10-H), 11.05 (1H,s,NH).

Workup

  1. temperatureunder reflux for 4 hours
  2. temperatureThe reaction mixture was cooled
  3. filtrationthe precipitated solid filtered off
  4. customRecrystallisation from DMF/ethanol

Sources & evidence

ORD record
ord-a95c86936b5f41709d21abaf83623448
Source dataset
uspto-grants-1988_07
Patent number
US04755511

Reaction notes

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