Hydrazine → HCID 55281930, compound

HRID 905602Notes

Reaction equation

HRID 905602 reaction equation
[CH2:1]1[CH:5]2[C:6]3[C:11]([CH:3]([CH2:4]2)[CH2:2]1)=[N:10][C:9](Cl)=[N:8][CH:7]=3.[NH2:13][NH2:14]>N1C=CC=CC=1>[CH2:1]1[CH:5]2[C:6]3[C:11]([CH:3]([CH2:4]2)[CH2:2]1)=[N:10][C:9]([NH:13][NH2:14])=[N:8][CH:7]=3

Participants

4

Reactant 2

HCID 9321HydrazineHCID 58513940HCID 58513940, compound

Product 1

HCID 55281930HCID 55281930, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-Chloro-5,8-methano-5,6,7,8-tetrahydroquinazoline was dissolved in anhydrous pyridine (30 mL) and treated with anhydrous hydrazine (15 mL) at 120° C. for 5 h. The solvent was removed under vacuum. The residue was partitioned between chloroform and 1M aqueous potassium carbonate solution. The organic layer was dried over anhydrous sodium sulfate and concentrated to give 2-hydrazino-5,8-methano-5,6,7,8-tetrahydroquinazoline as a tan solid, 2.68 g; 1H NMR (CDCl3, 300 MHz) 7.99 (s, 1H), 7.93 (br s, 1H), 3.90 (br s, 2H), 3.48 (s, 1H), 3.23 (s, 1H), 1.97 (m, 2H), 1.76 (d, 1H), 1.55 (d, 1H), 1.20-1.35 (m, 2H) ppm; 13C NMR (CDCl3, 75 MHz ) 179.48, 163.48, 147.10, 129.57, 47.58, 45.45, 39.86, 27.82, 25.46; MS(ES) 177 (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

Sources & evidence

ORD record
ord-f05f507afc134d2dabe3d423b00f950c
Source dataset
uspto-grants-2011_09
Patent number
US08012965B2

Reaction notes

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