Hydrochloric Acid → 1-(5-Bromo-1,2,3,4-tetrahydroquinoline-1-carbonyl)cyclopropanecarboxylic acid

HRID 2175297Notes

Reaction equation

HRID 2175297 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][CH2:6][N:7]2[C:12]([C:14]1([C:17]([O:19]C)=[O:18])[CH2:16][CH2:15]1)=[O:13].[Li+].[OH-].Cl>O1CCOCC1>[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][CH2:6][N:7]2[C:12]([C:14]1([C:17]([OH:19])=[O:18])[CH2:16][CH2:15]1)=[O:13]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 70982909Methyl 1-(5-bromo-1,2,3,4-tetrahydroquinoline-1-carbonyl)cyclopropanecarboxylate

Product 1

HCID 709824931-(5-Bromo-1,2,3,4-tetrahydroquinoline-1-carbonyl)cyclopropanecarboxylic acidYield 77.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of methyl 1-(5-bromo-1,2,3,4-tetrahydroquinoline-1-carbonyl)cyclopropanecarboxylate (500 mg, 1.478 mmol) and LiOH (1.478 mL, 5.91 mmol) in 1,4-dioxane (5 mL) was stirred at room temperature for 2 d, and then adjusted to pH 1-3 with 3 N HCl. The resulting mixture was extracted with ethyl acetate (3×15 ml). The combined organic layer was washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated to afford the title compound (0.37 g, 37%).

Workup

  1. extractionThe resulting mixture was extracted with ethyl acetate (3×15 ml)
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-421cc565f47b4c22ae498304b73e5b0e
Source dataset
uspto-grants-2015_06
Patent number
US09062028B2

Reaction notes

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