Hydrazine → HCID 135703158, compound

HRID 27767Notes

Reaction equation

HRID 27767 reaction equation
NN.[CH3:3][C:4]1[C:5]([N+:15]([O-])=O)=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[CH:9][NH:8][C:7]2=[O:14]>C(O)C.CN(C)C=O>[NH2:15][C:5]1[C:4]([CH3:3])=[CH:13][CH:12]=[C:11]2[C:6]=1[C:7](=[O:14])[NH:8][CH:9]=[N:10]2

Participants

5

Reactant 2

HCID 9321HydrazineHCID 135703156HCID 135703156, compound2×

Product 1

HCID 135703158HCID 135703158, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 6228DimethylformamideSolvent

Procedure

An aqueous hydrazine solution (83%, 10 ml) in ethanol (10 ml) was added carefully at 28° under a nitrogen atmosphere to a mixture of 6-methyl-5-nitroquinazoline-4-one (formula 16, prepared according to Example VI) (10.0 g, 490 m-mol) and palladium-one-charcoal (10%, 1.0 g) in ethanol (150 ml). The mixture was refluxed for 1 hour. Cooling of the mixture to room temperature yielded crystals which were dissolved in dimethyl formamide (150 ml) and separated from the catalyst by filtration. The filtrate was evaporated and the residue recrystallized from ethanol. This yielded 7.0 g (82%) of the formula 17 target compound in the form of light yellow crystals, m.p. 260°-261° (decomp.); ir (KBr): 3480, 3315 cm-1 (NH2); pmr (DMSO-d6): δ 2.13 (s, 3 CH3), 6.70 (d, 1, J=8.5 Hz, H7), 6.95 (m, 2, D2O-exchangeable NH2), 7.36 (d, 1, J=8.5 Hz, H8), 7.88 (s, 1, H2), 11.67 (m, 1, D2O-exchangeable NH); ms (70 eV): m/e 175 (100%, M+).

Workup

  1. temperatureThe mixture was refluxed for 1 hour
  2. customyielded crystals which
  3. customseparated from the catalyst by filtration
  4. customThe filtrate was evaporated
  5. customthe residue recrystallized from ethanol

Sources & evidence

ORD record
ord-b50506b08fd549fd8adbe8ac1119ccec
Source dataset
uspto-grants-1980_09
Patent number
US04223143

Reaction notes

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