HCID 135838127, compound → HCID 135838119, compound

HRID 381561Notes

Reaction equation

HRID 381561 reaction equation
O.S(O)(O)(=O)=O.[NH2:7][C:8]1[NH:17][C:16](=[O:18])[C:15]2[C:14]3[CH:19]=[CH:20][C:21]([N+:23]([O-])=O)=[CH:22][C:13]=3[CH2:12][CH2:11][C:10]=2[N:9]=1.[H][H]>[Pd].Cl.O>[NH2:7][C:8]1[NH:17][C:16](=[O:18])[C:15]2[C:14]3[CH:19]=[CH:20][C:21]([NH2:23])=[CH:22][C:13]=3[CH2:12][CH2:11][C:10]=2[N:9]=1

Participants

6

Reactant 2

HCID 135838127HCID 135838127, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 135838119HCID 135838119, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

A suspension of 3-amino-5,6-dihydro-8-nitrobenzo[f]quinazolin-1(2H)-one sulfate monohydrate (2.0 g, 5.3 mmoles) and 5% palladium on carbon (10 mg) in 1 N HCl (20 ml) was reacted with hydrogen using a Parr hydrogenation apparatus. When uptake of hydrogen ceased, the mixture was filtered and the filtrate was evaporated, leaving a white residue which was resuspended in water (20 ml) with stirring, and filtered. The crude product was recrystallized from 2 M H2SO4 to give, after drying, 3,8-diamino-5,6-dihydrobenzo[f]quinazolin-1(2H)-one as a white solid. (1.1 g, 61%) 1H NMR (DMSO-d6, 80 MHz) δ: 2.60-2.65(m, 4H, CH2CH2); 4.99-5.69(br s, 2H, NH2); 6.75-6.79(m, 4H, NH2+Ar); 8.24-8.35(d, J=9 Hz, 1H, Ar). Anal. Calculated for C12H12N4O.H2SO4.1/2H2O: C, 42.98; H, 4.51; N. 16.71; S, 9.56. Found: C, 42.95; H, 4.54; N. 16.66; S, 9.57.

Workup

  1. filtrationthe mixture was filtered
  2. customthe filtrate was evaporated
  3. customleaving a white residue which
  4. filtrationfiltered
  5. customThe crude product was recrystallized from 2 M H2SO4
  6. customto give
  7. customafter drying

Sources & evidence

ORD record
ord-5f6f321703f7452399b0035124ee3bfa
Source dataset
uspto-grants-2001_10
Patent number
US06306865B1

Reaction notes

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