Hydrazine → 5,6-Dihydro-3-hydrazinobenzo(H)cinnoline

HRID 531179Notes

Reaction equation

HRID 531179 reaction equation
Cl[C:2]1[N:3]=[N:4][C:5]2[C:6]3[CH:15]=[CH:14][CH:13]=[CH:12][C:7]=3[CH2:8][CH2:9][C:10]=2[CH:11]=1.[NH2:16][NH2:17]>N1C=CC=CC=1>[NH:16]([C:2]1[N:3]=[N:4][C:5]2[C:6]3[CH:15]=[CH:14][CH:13]=[CH:12][C:7]=3[CH2:8][CH2:9][C:10]=2[CH:11]=1)[NH2:17]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 104433233-Chloro-5,6-dihydrobenzo[h]cinnoline

Product 1

HCID 323445,6-Dihydro-3-hydrazinobenzo(H)cinnoline

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3-Chloro-5,6-dihydrobenzo[h]cinnoline was heated at 100° C. in a mixture of anhydrous pyridine (30 mL) and anhydrous hydrazine (5 mL) for 3.25 h. The solvent was removed under vacuum and the residue was partitioned between chloroform and 1M aqueous potassium carbonate solution. The organic layer was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was triturated with diethyl ether and filtered to give 3-hydrazinyl-5,6-dihydrobenzo[h]cinnoline as a beige solid; 1H NMR (DMSO-d6, 300 MHz) 8.17 (d, 1H), 7.91 (br s, 1H), 7.28 (m, 3H), 6.87 (s, 1H), 4.34 (br s, 2H), 2.92 (m, 4H) ppm; 13C NMR (DMSO-d6, 75 MHz) 162.49, 147.92, 137.95, 137.39, 132.97, 128.87, 128.75, 127.56, 123.59, 110.55, 28.01, 27.66; MS (ES) 213 (M+H).

Workup

  1. customThe solvent was removed under vacuum
  2. customthe residue was partitioned between chloroform and 1M aqueous potassium carbonate solution
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under vacuum
  5. customThe residue was triturated with diethyl ether
  6. filtrationfiltered

Sources & evidence

ORD record
ord-5a2b21cf1bfc47ec8b6343d441b37fd4
Source dataset
uspto-grants-2016_05
Patent number
US09353126B2

Reaction notes

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