Ethanol → 103603-13-0

HRID 845068Notes

Reaction equation

HRID 845068 reaction equation
C([NH:4][C:5]1[CH:6]=[CH:7][C:8]2[C:17]3[CH:12]([CH2:13][C:14](=[O:18])[NH:15][N:16]=3)[CH2:11][CH2:10][C:9]=2[CH:19]=1)(=O)C.C(O)C>O.NN>[NH2:4][C:5]1[CH:6]=[CH:7][C:8]2[C:17]3[CH:12]([CH2:13][C:14](=[O:18])[NH:15][N:16]=3)[CH2:11][CH2:10][C:9]=2[CH:19]=1

Participants

4

Reactant 2

HCID 702EthanolHCID 219045Brn 6572492

Product 1

HCID 13603301103603-13-0Yield 42.7%

Reagents, catalysts & solvents 1

HCID 24654Hydrazine hydrate (1:1)Solvent

Procedure

8-Acetamido-4,4a,5,6-tetrahydrobenzo[h]cinnolin-3[2H]-one (0.7 g) was suspended in hydrazine hydrate (13 ml) and ethanol (2 ml) and heated under reflux for 2 hours. The hot solution was filtered through diatomaceous earth and the filtrate extracted with chloroform. Evaporation of the dried (MgSO4) extract gave a gum which was crystallised by trituration with 1-propanol. The crude solid was fractionated by flash chromatography (CHCl3 eluant) and from the appropriate fraction was obtained 8-amino-4,4a,5,6-tetrahydrobenzo[h]cinnolin-3[2H]-one (0.25 g; m.p. 290-1° from n-propanol/water)ν(Nujol mull) 3465, 3350, 3230, 1658, 1617, 1585 cm-1 ; δ(DMSO-d6) 1.2-1.7 (1H,m,5-H), 1.8-2.9 (6H,m,4,4a,5,6-H) 5.35 (2H,s,NH2), 6.34 (1H,m,7-H), 6.46 (1H,m,9-H), 7.66 (1H,d,10-H), 10.5 (1H,s,NHCO) M+ 215.

Workup

  1. temperatureunder reflux for 2 hours
  2. filtrationThe hot solution was filtered through diatomaceous earth
  3. extractionthe filtrate extracted with chloroform
  4. customEvaporation of the
  5. dry with materialdried (MgSO4)
  6. extractionextract
  7. customgave a gum which
  8. customwas crystallised by trituration with 1-propanol

Sources & evidence

ORD record
ord-ef205812d93f4b20a01a4ae4035c23af
Source dataset
uspto-grants-1988_07
Patent number
US04755511

Reaction notes

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