Tin tetrachloride → HCID 21936647, compound

HRID 1241721Notes

Reaction equation

HRID 1241721 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([N:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][N:18]=3)[CH:13]=[C:12]([CH2:20][CH2:21][CH:22]([OH:29])[C:23]3[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=3)[C:11]2=[O:30])[CH:7]=[CH:8][CH:9]=1)([O-])=O.[Sn](Cl)(Cl)(Cl)Cl>>[NH2:1][C:4]1[CH:5]=[C:6]([N:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][N:18]=3)[CH:13]=[C:12]([CH2:20][CH2:21][CH:22]([OH:29])[C:23]3[CH:24]=[CH:25][N:26]=[CH:27][CH:28]=3)[C:11]2=[O:30])[CH:7]=[CH:8][CH:9]=1

Participants

3

Reactant 2

HCID 24287Tin tetrachlorideHCID 21936644HCID 21936644, compound

Product 1

HCID 21936647HCID 21936647, compoundYield 65.1%

Procedure

The procedure of Example 19 was repeated using 1-(3-nitrophenyl)-3-[3-hydroxy-3-(pyridin-4-yl)propyl]-1,8-naphthyridin-2(1H)-one (400 mg, 0.99 mmol; prepared in Example 20) and tin chloride.2H2O (2 g, 5-fold weights) while ice-cooling to obtain 1-(3-aminophenyl)-3-[3-hydroxy-3-(pyridin-4-yl)propyl]-1,8-naphthyridin-2(1H)-one (240 mg, 65%; mp 209–211° C.).

Workup

  1. temperature2H2O (2 g, 5-fold weights) while ice-cooling

Sources & evidence

ORD record
ord-196b598f6df4456cbf4779d28e32083b
Source dataset
uspto-grants-2006_10
Patent number
US07115623B2

Reaction notes

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