Ammonium formate → 4-(6-Chloro-2,3-dihydro-indol-1-yl)-quinazolin-7-yl amine hydrochloride

HRID 1597987Notes

Reaction equation

HRID 1597987 reaction equation
Cl.[Cl:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH2:8][N:9]2[C:12]2[C:21]3[C:16](=[CH:17][C:18]([N+:22]([O-])=O)=[CH:19][CH:20]=3)[N:15]=[CH:14][N:13]=2)=[CH:5][CH:4]=1.C([O-])=O.[NH4+]>C(O)C>[ClH:2].[Cl:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH2:8][N:9]2[C:12]2[C:21]3[C:16](=[CH:17][C:18]([NH2:22])=[CH:19][CH:20]=3)[N:15]=[CH:14][N:13]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 2723923Ammonium formateHCID 189328314-(6-Chloro-2,3-dihydro-indol-1-yl)-7-nitro-quinazoline hydrochloride

Product 1

HCID 189328104-(6-Chloro-2,3-dihydro-indol-1-yl)-quinazolin-7-yl amine hydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-(6-Chloro-2,3-dihydro-indol-1-yl)-7-nitro-quinazoline hydrochloride (2.16 g, 5.90 mmol) was slurried in 250 mL of ethanol containing 0.21 g of 10% paladium on carbon and treated with ammonium formate (1.68 g, 26.6 mmol). After 16 hours the mixture was filtered through celite and evaporated in vacuo to a residue. This was dissolved in chloroform, filtered and washed with sodium bicarbonate and brine then dried with magnesium sulfate, filtered and evaporated in vacuo to give crude product which was recrystallized from 50% aqueous ethanol. The solid was dissolved in methanol containing anhydrous hydrogen chloride and poured into ether to yield the title compound after filtration and drying in vacuo; 0.687 g (35%) M.P. 282°-283° C.

Workup

  1. filtrationAfter 16 hours the mixture was filtered through celite
  2. customevaporated in vacuo to a residue
  3. dissolutionThis was dissolved in chloroform
  4. filtrationfiltered
  5. washwashed with sodium bicarbonate and brine
  6. dry with materialthen dried with magnesium sulfate
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customto give crude product which
  10. customwas recrystallized from 50% aqueous ethanol
  11. dissolutionThe solid was dissolved in methanol containing anhydrous hydrogen chloride
  12. additionpoured into ether

Sources & evidence

ORD record
ord-2961a7e29f8a4229a87c8a08638cf956
Source dataset
uspto-grants-1998_04
Patent number
US05736534

Reaction notes

Loading…