Stannous Chloride → HCID 19087667, compound

HRID 1464287Notes

Reaction equation

HRID 1464287 reaction equation
[C:1]1([C:7]2[CH2:8][CH2:9][N:10]([CH2:13][CH2:14][CH2:15][CH2:16][N:17]3[C:26]4[C:21](=[CH:22][CH:23]=[C:24]([N+:27]([O-])=O)[CH:25]=4)[C:20](=[O:30])[NH:19][C:18]3=[O:31])[CH2:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Sn](Cl)[Cl:33]>C(O)C>[ClH:33].[C:1]1([C:7]2[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][CH2:15][CH2:16][N:17]3[C:26]4[C:21](=[CH:22][CH:23]=[C:24]([NH2:27])[CH:25]=4)[C:20](=[O:30])[NH:19][C:18]3=[O:31])[CH2:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 19087706HCID 19087706, compound

Product 1

HCID 19087667HCID 19087667, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred suspension of 1-[4-(4-phenyl-1,2,3,6-tetrahydropyridin-1-yl)butyl]-7-nitro-2,4(1H,3H)-quinazolinedione (840 mg) in dry ethanol (30 ml) was added tin(II) chloride (1.90 g) at 80° C. After stirring for 3 hours, the mixture was quenched with 2N potassium hydroxide, diluted with chloroform. The organic layer was decanted and the residue was washed with chloroform. Combined organic layer was dried over magnesium sulfate and evaporated. 1-[4-(4-Phenyl-1,2,3,6-tetrahydropyridin-1-yl)butyl]-7-amino-2,4(1H,3H)-quinazolinedione hydrochloride (546 mg) as a crystal was obtained by recrystallization from 10% hydrogen chloride in methanol.

Workup

  1. customthe mixture was quenched with 2N potassium hydroxide
  2. additiondiluted with chloroform
  3. customThe organic layer was decanted
  4. washthe residue was washed with chloroform
  5. dry with materialCombined organic layer was dried over magnesium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-985c1958248f4ebcb09478098c16b008
Source dataset
uspto-grants-1994_04
Patent number
US05304560

Reaction notes

Loading…