Hydrazine hydrate (1:1) → 2,4,4A,5,6,7-Hexahydro-benzo[6,7]cyclohepta[1,2-C]pyridazin-3-one

HRID 400406Notes

Reaction equation

HRID 400406 reaction equation
O=[C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][CH2:5][CH2:4][CH:3]1[CH2:13][C:14]([OH:16])=O.O.[NH2:18][NH2:19]>C(O)C>[N:18]1[NH:19][C:14](=[O:16])[CH2:13][CH:3]2[CH2:4][CH2:5][CH2:6][C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[C:2]=12

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 3445076,7,8,9-Tetrahydro-5-oxo-5H-benzocycloheptene-6-acetic acid

Product 1

HCID 147375392,4,4A,5,6,7-Hexahydro-benzo[6,7]cyclohepta[1,2-C]pyridazin-3-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of the compound of formula (Dc), 2-(5-oxo-6,7,8,9-tetrahydro-5H-benzo[7]annulen-6-yl)acetic acid, (5.7 g, 26.1 mmol) and hydrazine hydrate (1.6 mL, 32.7 mmol) in 20 mL of ethanol was refluxed for 2 h, cooled and filtered (washed with small amount of EtOH) to give the compound of formula (Dd), 4a,5,6,7-tetrahydro-2H-benzo[6,7]cyclohepta[c]pyridazin-3(4H)-one, as a white solid (4.7 g, 84%); 1H NMR (300 MHz, CDCl3) δ: 8.61 (bs, 1H), 7.53-7.14 (m, 4H), 2.98-2.75 (m, 3H), 2.58 (dd, J=15.3, 16.8 Hz, 1H), 2.31 (dd, J=12.0, 16.8 Hz, 1H), 1.96-1.59 (m, 4H); LC-MS: purity: 100%; MS (m/e): 215 (MH+).

Workup

  1. temperaturewas refluxed for 2 h
  2. temperaturecooled
  3. filtrationfiltered
  4. wash(washed with small amount of EtOH)

Sources & evidence

ORD record
ord-427fc9923a4147818b30232271106c37
Source dataset
uspto-grants-2014_06
Patent number
US08741898B2

Reaction notes

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