2-Methyl-2-butene → 6-(2-Tert-butoxy-2-oxoethoxy)-2-chloroquinoline-3-carboxylic acid

HRID 2403689Notes

Reaction equation

HRID 2403689 reaction equation
[Cl:1][C:2]1[C:11]([CH:12]=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:14][CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH:8]=2)[N:3]=1.CC(=CC)C.Cl([O-])=[O:29].[Na+].P([O-])(O)(O)=O.[Na+]>C(O)(C)(C)C.O>[C:19]([O:18][C:16](=[O:17])[CH2:15][O:14][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[N:3]=[C:2]([Cl:1])[C:11]([C:12]([OH:29])=[O:13])=[CH:10]2)([CH3:22])([CH3:21])[CH3:20]

Participants

7

Reactant 4

HCID 105532-Methyl-2-buteneHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphateHCID 86672868Tert-butyl 2-(2-chloro-3-formylquinolin-6-yloxy)acetate

Product 1

HCID 866728696-(2-Tert-butoxy-2-oxoethoxy)-2-chloroquinoline-3-carboxylic acidYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

To a suspension of tert-butyl 2-(2-chloro-3-formylquinolin-6-yloxy)acetate (3.6 g, 11 mmol) in tert-butanol (150 mL) was added 2-methyl-2-butene (14.9 mL, 133 mmol) and a solution of sodium chlorite (8.27 g, 73.1 mmol) and sodium dihydrogenphosphate (8.10 g, 58.7 mmol) in water (50 mL). The reaction was allowed to stir at room temperature for 1 hour. The tert-butanol was removed in vacuo. The mixture was diluted with water (60 mL) and acidified to pH=4 with 1 N aqueous hydrochloric acid. The resulting precipitate was filtered, washed with water, and dried under vacuum to give the title compound (3.7 g, 100%) as a white solid. +ESI (M+H) 338.1; 1H NMR (400 MHz, CD3OD, δ): 8.69 (s, 1 H), 7.89 (d, J=9.19 Hz, 1 H), 7.56 (dd, J=9.19, 2.74 Hz, 1 H), 7.34 (d, J=2.93 Hz, 1 H), 4.76 (s, 2 H), 1.49 (s, 9 H).

Workup

  1. customThe tert-butanol was removed in vacuo
  2. additionThe mixture was diluted with water (60 mL)
  3. filtrationThe resulting precipitate was filtered
  4. washwashed with water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-4f6f13e0afac41cb82b506af9d9fbece
Source dataset
uspto-grants-2014_08
Patent number
US08802688B2

Reaction notes

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