Ammonium formate → HCID 136210639, compound

HRID 412030Notes

Reaction equation

HRID 412030 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([C:8](=[O:24])[NH:9][C:10]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[O:20][CH2:21][CH2:22][CH3:23])=[N:11]2)=[CH:6][CH:5]=1)([O-])=O.C([O-])=O.[NH4+]>CO.[Pd]>[NH2:1][C:4]1[CH:13]=[C:12]2[C:7]([C:8](=[O:24])[NH:9][C:10]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[O:20][CH2:21][CH2:22][CH3:23])=[N:11]2)=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 136134543HCID 136134543, compound

Product 1

HCID 136210639HCID 136210639, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A stirred solution of 7-nitro-2-(2-propoxyphenyl)-4(3H)-quinazolinone (3.0 g) in dry methanol (450 ml) was treated sequentially under a carbon dioxide atmosphere with 5% Pd/C(1.5 g) and anhydrous ammonium formate (2.8 g). After 60 minutes solids were removed by filtration and the filtrate evaporated to dryness. The residue was partitioned between water and dichloromethane, the organic layer separated, dried (magnesium sulphate) and evaporated. The residue was recrystallized from diethyl ether-petroleum ether to give 7-amino-2-(2-propoxyphenyl)-4(3H)-quinazolinone, 2.7 g, m.p. 185° C.

Workup

  1. customAfter 60 minutes solids were removed by filtration
  2. customthe filtrate evaporated to dryness
  3. customThe residue was partitioned between water and dichloromethane
  4. customthe organic layer separated
  5. dry with materialdried (magnesium sulphate)
  6. customevaporated
  7. customThe residue was recrystallized from diethyl ether-petroleum ether

Sources & evidence

ORD record
ord-07c28428eabc423f9141324218326c2f
Source dataset
uspto-grants-2003_05
Patent number
US06562830B1

Reaction notes

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