Stannous chloride dihydrate → HCID 49846267, compound

HRID 1926694Notes

Reaction equation

HRID 1926694 reaction equation
[NH2:1][CH:2]1[CH2:11][C:10]2[C:5](=[CH:6][C:7]([Br:12])=[CH:8][CH:9]=2)[N:4]([OH:13])[C:3]1=[O:14].Cl.NC(CC1C=CC(Br)=CC=1[N+]([O-])=O)C(O)=O.O.O.[Sn](Cl)Cl>CCO>[NH2:1][C@@H:2]1[CH2:11][C:10]2[C:5](=[CH:6][C:7]([Br:12])=[CH:8][CH:9]=2)[N:4]([OH:13])[C:3]1=[O:14]

Participants

5

Reactant 3

HCID 61436Stannous chloride dihydrateHCID 1276138382420-39-1HCID 12761396HCID 12761396, compound

Product 1

HCID 49846267HCID 49846267, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-Amino-7-bromo-1-hydroxy-3,4-dihydroquinolin-2(1H)-one (26) To a solution of 2-amino-3-(4-bromo-2-nitrophenyl)propanoic acid, hydrochloride salt (25) (343 mg, 1.06 mmol) in EtOH (10 mL) was added tin(II) chloride dihydrate (541 mg, 2.40 mmol), and the reaction was stirred at RT overnight. It was then quenched with aqueous ammonium hydroxide (1.5 mL), and the resulting precipitate was removed via filtration and washed with MeOH. The combined filtrates were concentrated in vacuo, and the residue was purified by chromatography on silica gel to provide the title product as a white powder (161 mg, 58%). LCMS m/z 258.9 (M+1). 1H NMR (500 MHz, DMSO-d6) δ 2.71 (dd, J=15.4, 12.9 Hz, 1H) 2.99 (dd, J=15.6, 6.1 Hz, 1H), 3.56 (dd, J=12.8, 6.0 Hz, 1H) 7.17-7.21 (m, 2H), 7.28 (d, J=1.7 Hz, 1H).

Workup

  1. customIt was then quenched with aqueous ammonium hydroxide (1.5 mL)
  2. customthe resulting precipitate was removed via filtration
  3. washwashed with MeOH
  4. concentrationThe combined filtrates were concentrated in vacuo
  5. customthe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-ba238dab1562458899952cdbcefe817a
Source dataset
uspto-grants-2012_05
Patent number
US08183238B2

Reaction notes

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