Hydrazine → 2-Hydrazino-5,6-dihydrobenzo[h]quinazoline

HRID 531177Notes

Reaction equation

HRID 531177 reaction equation
Cl[C:2]1[N:11]=[CH:10][C:9]2[CH2:8][CH2:7][C:6]3[CH:12]=[CH:13][CH:14]=[CH:15][C:5]=3[C:4]=2[N:3]=1.[NH2:16][NH2:17]>N1C=CC=CC=1>[NH:16]([C:2]1[N:11]=[CH:10][C:9]2[CH2:8][CH2:7][C:6]3[CH:12]=[CH:13][CH:14]=[CH:15][C:5]=3[C:4]=2[N:3]=1)[NH2:17]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 534860272-Chloro-5,6-dihydrobenzo[h]quinazoline

Product 1

HCID 597745152-Hydrazino-5,6-dihydrobenzo[h]quinazoline

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Crude 2-chloro-5,6-dihydrobenzo[h]quinazoline was heated at 120° C. in a mixture of anhydrous pyridine (20 mL) and anhydrous hydrazine (7 mL) for 4 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 to give 2-hydrazinyl-5,6-dihydrobenzo[h]quinazoline as a white solid, 2.16 g. 1H NMR (CDCl3, 300 MHz) 8.27 (d, 1H), 8.20 (s, 1H), 7.35 (m, 2H), 7.21 (d, 1H), 6.42 (s, 1H), 4.00 (br s, 2H), 2.91 (m, 2H), 2.80 (m, 2H) ppm; 13C NMR (CDCl3, 75 MHz) 164.29, 160.00, 156.72, 139.87, 132.83, 131.02, 128.25, 127.25, 125.47, 119.03, 28.54, 24.24; 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

Sources & evidence

ORD record
ord-d6ba9eb7f87a43808d00ba41e8463c4f
Source dataset
uspto-grants-2016_05
Patent number
US09353126B2

Reaction notes

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