Ethanol → 103422-53-3

HRID 845058Notes

Reaction equation

HRID 845058 reaction equation
C([NH:4][C:5]1[CH:6]=[C:7]2[C:16](=[CH:17][CH:18]=1)[C:10]1=[N:11][NH:12][C:13](=[O:15])[CH2:14][CH:9]1[CH2:8]2)(=O)C.C(O)C>O.NN>[NH2:4][C:5]1[CH:6]=[C:7]2[C:16](=[CH:17][CH:18]=1)[C:10]1=[N:11][NH:12][C:13](=[O:15])[CH2:14][CH:9]1[CH2:8]2

Participants

4

Reactant 2

HCID 702EthanolHCID 13603296103422-54-4

Product 1

HCID 357997103422-53-3Yield 33%

Reagents, catalysts & solvents 1

HCID 24654Hydrazine hydrate (1:1)Solvent

Procedure

7-Acetamido-4,4a-dihydro-[5H]-indeno[1,2-c]pyridazin-3[2H]-one (1.50 g) was suspended in hydrazine hydrate (30 ml ) and heated under reflux with ethanol (5 ml ) for 2 hours. The solution was filtered through diatomaceous earth, allowed to cool, then extracted into chloroform. The combined organic extracts were dried over magnesium sulphate and concentrated. Recrystallisation of the crude product from n-propanol gave 7-amino-4,4a-dihydro-[5H]-indeno[1,2-c]pyridazin-3[2H]-one (0.41 g, m.p. 244°-245° C.) as a pale yellow powder; ν(Nujol mull) 3400, 3320, 3220, 1652, 1635, 1600, and 1580cm-1 ; δ(DMSO-d6) 2.50 (3H,m,4-H,5-H2), 3.05 (1H,m,4a-H), 5.67 (2H,s(br),NH2), 6.55 (2H,m,6,H-H), 7.27 (1H,d,9-H).

Workup

  1. temperatureheated
  2. filtrationThe solution was filtered through diatomaceous earth
  3. temperatureto cool
  4. extractionextracted into chloroform
  5. dry with materialThe combined organic extracts were dried over magnesium sulphate
  6. concentrationconcentrated
  7. customRecrystallisation of the crude product from n-propanol

Sources & evidence

ORD record
ord-22cc40852bda433eb02bebe7aea728c0
Source dataset
uspto-grants-1988_07
Patent number
US04755511

Reaction notes

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