Stannane, hydroxytrimethyl- → 2-(7-cyano-2-oxoquinolin-1(2H)-yl)acetic acid

HRID 2098012Notes

Reaction equation

HRID 2098012 reaction equation
[OH-].C[Sn+](C)C.[C:6]([C:8]1[CH:17]=[C:16]2[C:11]([CH:12]=[CH:13][C:14](=[O:23])[N:15]2[CH2:18][C:19]([O:21]C)=[O:20])=[CH:10][CH:9]=1)#[N:7]>ClCCCl.ClCCl>[C:6]([C:8]1[CH:17]=[C:16]2[C:11]([CH:12]=[CH:13][C:14](=[O:23])[N:15]2[CH2:18][C:19]([OH:21])=[O:20])=[CH:10][CH:9]=1)#[N:7]

Participants

5

Reactant 2

HCID 11217597Stannane, hydroxytrimethyl-HCID 68785451methyl 2-(7-cyano-2-oxoquinolin-1(2H)-yl)acetate

Product 1

HCID 687822352-(7-cyano-2-oxoquinolin-1(2H)-yl)acetic acidYield 89%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

Trimethyl tin hydroxide (0.388 g, 2.14 mmol) was added to a solution of methyl 2-(7-cyano-2-oxoquinolin-1(2H)-yl)acetate (0.104 g, 0.429 mmol) in 1,2-dichloroethane (5 mL) and the resulting suspension was stirred at reflux for 4 h. The reaction mixture was diluted with dichloromethane and washed with 1N aqueous HCl. Filtration of the organic phase provided 87 mg (89%) of 2-(7-cyano-2-oxoquinolin-1(2H)-yl)acetic acid. Retention time (min)=0.987, method [1], MS (ESI) 229.1 (M+H).

Workup

  1. temperatureat reflux for 4 h
  2. washwashed with 1N aqueous HCl
  3. filtrationFiltration of the organic phase

Sources & evidence

ORD record
ord-143eea475eb64ecda7d581989e23bab5
Source dataset
uspto-grants-2013_05
Patent number
US08450363B2

Reaction notes

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