Hydrazine → 3-Hydrazino-6,7-dihydro-5h-benzo[6,7]cyclohepta[1,2-c]pyridazine

HRID 1749337Notes

Reaction equation

HRID 1749337 reaction equation
Cl[C:2]1[N:7]=[N:6][C:5]2[C:8]3[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=3[CH2:10][CH2:11][CH2:12][C:4]=2[CH:3]=1.[NH2:17][NH2:18]>C(O)C>[NH:17]([C:2]1[N:7]=[N:6][C:5]2[C:8]3[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=3[CH2:10][CH2:11][CH2:12][C:4]=2[CH:3]=1)[NH2:18]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 141261595-Chloro-3,4-diazatricyclo(9.4.0.0,2,7)pentadeca-1(15),2(7),3,5,11,13-hexaene

Product 1

HCID 592955463-Hydrazino-6,7-dihydro-5h-benzo[6,7]cyclohepta[1,2-c]pyridazine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Alternatively, 3-chloro-6,7-dihydro-5H-benzo[6,7]cyclohepta[1,2-c]pyridazine (1.6 g) was heated with anhydrous hydrazine (4 mL) in ethanol (50 mL) at 100° C. for 4.75 h. The solvent was removed under vacuum. The residue was partitioned between chloroform and 1M saturated aqueous potassium carbonate. The organic layer was dried over anhydrous sodium sulfate and concentrated under vacuum to give 3-hydrazino-6,7-dihydro-5H-benzo[6,7]cyclohepta[1,2-c]pyridazine as a brown solid; 1H NMR (CDCl3, 300 MHz) 7.74 (m, 1H), 7.30 (m, 2H), 7.17 (m, 1H), 6.92 (s, 1H), 2.49 (m, 2H), 2.39 (m, 2H), 2.12 (m, 2H) ppm; MS (ES) 227 (M+H).

Workup

  1. customThe solvent was removed under vacuum
  2. customThe residue was partitioned between chloroform and 1M saturated aqueous potassium carbonate
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-2479ebc650e843ebb18b15f28e71fc2e
Source dataset
uspto-grants-2015_10
Patent number
US09156820B2

Reaction notes

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