Water → HCID 178507606, compound

HRID 1822248Notes

Reaction equation

HRID 1822248 reaction equation
[CH2:1]([C:8]1[C:12]2[C:13](=[O:30])[N:14]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([N+:27]([O-])=O)[CH:22]=3)[C:15]3[N:16]=[CH:17][CH:18]=[CH:19][C:20]=3[C:11]=2[NH:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Sn](Cl)(Cl)(Cl)Cl.O.C(=O)([O-])[O-].[Na+].[Na+]>Cl>[NH2:27][C:23]1[CH:22]=[C:21]([N:14]2[C:15]3[N:16]=[CH:17][CH:18]=[CH:19][C:20]=3[C:11]3[NH:10][N:9]=[C:8]([CH2:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)[C:12]=3[C:13]2=[O:30])[CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 24287Tin tetrachlorideHCID 178514871HCID 178514871, compound

Product 1

HCID 178507606HCID 178507606, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To a solution of 3-benzyl-5-(3-nitrophenyl)-1H-pyrazolo[4,3-c][1,8]naphthyridin-4 (5H)-one (98 mg, 0.25 mmol) in conc. hydrochloric acid (7 ml) was added tin chloride.2H2O (500 mg, 5-fold weights), and the mixture was stirred at room temperature for 1.5 hour, admixed with water, then treated with sodium carbonate to make it to pH8-9, and extracted with chloroform 8 times. The organic layer was dried over anhydrous magnesium sulfate, and evaporated to give 5-(3-aminophenyl)-3-benzyl-1H-pyrazolo[4,3-c][1,8]naphthyridin-4 (5H)-one (63 mg, 70%).

Workup

  1. extractionextracted with chloroform 8 times
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-2601cf496df74d6b8ccec12eaf7041e1
Source dataset
uspto-grants-2009_10
Patent number
US07608716B2

Reaction notes

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