Stannous chloride dihydrate → 2-{2-[6-Amino-7-chloro-3-(3,5-dimethylphenyl)-2-oxo-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid benzyl ester

HRID 1858065Notes

Reaction equation

HRID 1858065 reaction equation
O.O.[Sn](Cl)Cl.[CH2:6]([O:13][C:14]([N:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH:17]1[CH2:22][CH2:23][O:24][C:25]1[C:34]2[C:29](=[CH:30][C:31]([Cl:38])=[C:32]([N+:35]([O-])=O)[CH:33]=2)[NH:28][C:27](=[O:39])[C:26]=1[C:40]1[CH:45]=[C:44]([CH3:46])[CH:43]=[C:42]([CH3:47])[CH:41]=1)=[O:15])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>>[CH2:6]([O:13][C:14]([N:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH:17]1[CH2:22][CH2:23][O:24][C:25]1[C:34]2[C:29](=[CH:30][C:31]([Cl:38])=[C:32]([NH2:35])[CH:33]=2)[NH:28][C:27](=[O:39])[C:26]=1[C:40]1[CH:45]=[C:44]([CH3:46])[CH:43]=[C:42]([CH3:47])[CH:41]=1)=[O:15])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

3

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 544370152-{2-[6-Nitro-7-chloro-3-(3,5-dimethylphenyl)-2-oxo-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid benzyl ester

Product 1

HCID 539323332-{2-[6-Amino-7-chloro-3-(3,5-dimethylphenyl)-2-oxo-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid benzyl esterYield 47.5%

Conditions

Temperature
70 °C

Procedure

To a solution of 2-{2-[6-nitro-7-chloro-3-(3,5-dimethylphenyl)-2-oxo-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid benzyl ester (1.11 g in 30 mL ethanol) was added 2 mL tin(II)cloride dihydrate and the mixture heated to 70° C. on an oil bath. After 2 hours, the reaction was cooled to room temperature and quenched by the addition of 300 mL ice-water. The acidity of the resulting solution was adjusted to pH 8 by the addition of saturated aqueous sodium bicarbonate and the mixture extracted (2×) with ethyl acetate. The combined organics were washed with brine, dried over sodium sulfate and concentrated in vacuo. Purification of the crude oil by flash chromatography on silica gel (methylene chloride:ethyl acetate, 95:5) gave the title compound (0.50 g).

Workup

  1. temperaturethe reaction was cooled to room temperature
  2. customquenched by the addition of 300 mL ice-water
  3. additionThe acidity of the resulting solution was adjusted to pH 8 by the addition of saturated aqueous sodium bicarbonate
  4. extractionthe mixture extracted (2×) with ethyl acetate
  5. washThe combined organics were washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customPurification of the crude oil by flash chromatography on silica gel (methylene chloride:ethyl acetate, 95:5)

Sources & evidence

ORD record
ord-c94891cedfb349a58afe944a0e16e198
Source dataset
uspto-grants-2000_11
Patent number
US06150352

Reaction notes

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