Water → 7-Hydroxy-6-methoxy-4-(2,3-methylenedioxyanilino)quinazoline

HRID 1371476Notes

Reaction equation

HRID 1371476 reaction equation
Cl.C([O:9][C:10]1[CH:19]=[C:18]2[C:13]([C:14]([NH:20][C:21]3[CH:26]=[CH:25][CH:24]=[C:23]4[O:27][CH2:28][O:29][C:22]=34)=[N:15][CH:16]=[N:17]2)=[CH:12][C:11]=1[O:30][CH3:31])C1C=CC=CC=1.C([O-])=O.[NH4+].O>[Pd].CN(C=O)C>[OH:9][C:10]1[CH:19]=[C:18]2[C:13]([C:14]([NH:20][C:21]3[CH:26]=[CH:25][CH:24]=[C:23]4[O:27][CH2:28][O:29][C:22]=34)=[N:15][CH:16]=[N:17]2)=[CH:12][C:11]=1[O:30][CH3:31]

Participants

6

Reactant 3

HCID 962WaterHCID 2723923Ammonium formateHCID 219360977-Benzyloxy-6-methoxy-4-(2,3-methylenedioxyanilino)quinazoline hydrochloride

Product 1

HCID 1355941137-Hydroxy-6-methoxy-4-(2,3-methylenedioxyanilino)quinazolineYield 100.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 7-benzyloxy-6-methoxy-4-(2,3-methylenedioxyanilino)quinazoline hydrochloride (21 g), ammonium formate (30.2 g), 10% palladium-on-charcoal catalyst (4.8 g), water (26 ml) and DMF (350 ml) was stirred at ambient temperature for 2 hours. The mixture was filtered and the filtrate was evaporated. The residual oil was triturated under diethyl ether. The solid so obtained was triturated under water, collected by filtration, washed with water and with diethyl ether and dried under vacuum over phosphorus pentoxide. The material so obtained was purified by column chromatography on silica using a 9:1 mixture of methylene chloride and methanol as eluent. There was thus obtained the title compound (15 g); NMR Spectrum: (DMSOd6) 3.95 (s, 3H), 6.0 (s, 2H), 6.85 (m, 2H), 6.95 (d, 1H), 7.05 (s, 1H), 7.8 (s, 1H), 8.3 (s, 1H), 9.4 (s, 1H), 10.3 (s, 1H); Mass Spectrum: M+H+ 312.

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate was evaporated
  3. customThe residual oil was triturated under diethyl ether
  4. customThe solid so obtained
  5. customwas triturated under water
  6. filtrationcollected by filtration
  7. washwashed with water and with diethyl ether
  8. dry with materialdried under vacuum over phosphorus pentoxide
  9. customThe material so obtained
  10. customwas purified by column chromatography on silica using
  11. additiona 9:1 mixture of methylene chloride and methanol as eluent

Sources & evidence

ORD record
ord-77491d44b5eb4693b45fe34e8755fe37
Source dataset
uspto-grants-2007_01
Patent number
US07157467B2

Reaction notes

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