Hydrazine hydrate (1:1) → 121866-02-2

HRID 845064Notes

Reaction equation

HRID 845064 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=O)[CH:8]([CH2:14][C:15]([OH:17])=O)[CH2:7][CH2:6]2)#[N:2].O.[NH2:19][NH2:20]>C(O)(=O)C>[C:1]([C:3]1[CH:12]=[CH:11][C:10]2[C:9]3[CH:8]([CH2:14][C:15](=[O:17])[NH:19][N:20]=3)[CH2:7][CH2:6][C:5]=2[CH:4]=1)#[N:2]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 14853002HCID 14853002, compound

Product 1

HCID 3078592121866-02-2

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 6-cyano-1-oxo-1,2,3,4-tetrahydro-2-naphthyl acetic acid (5.0 g) in 50% hot aqueous acetic acid was treated with hydrazine hydrate (1.0 ml ) and heated under reflux for 2 hours. The precipitated solid was filtered off and washed with water to give 8-cyano-4,4a,5,6-tetrahydrobenzo[h]cinnolin-3[2H]-one (1.2 g; m.p. 292°-5°); ν(Nujol mull) 3500, 3225, 2225, 1685, 1615, and 1586; δ(DMSO-d6) 1.55 (1H,m,5-H), 2.14 (1H,m,5-H) 2.40 (2H,m,4-H), 2.78 (3H,m,4a,6-H), 7.65 (lH,m,9-H), 7.71 (lH, s, 7-H), 8.12 (1H,d,10-H), 11.04 (1H,s,NH).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 2 hours
  3. filtrationThe precipitated solid was filtered off
  4. washwashed with water

Sources & evidence

ORD record
ord-3dbb3215c9f04b8ea61ef5cf9615884d
Source dataset
uspto-grants-1988_07
Patent number
US04755511

Reaction notes

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