Sodium Hydroxide → (+/-)-4-(4,4,4-Trifluoro-1-(quinolin-3-ylamino)butyl)benzoic acid

HRID 1424283Notes

Reaction equation

HRID 1424283 reaction equation
[F:1][C:2]([F:29])([F:28])[CH2:3][CH2:4][CH:5]([C:17]1[CH:27]=[CH:26][C:20]([C:21]([O:23]CC)=[O:22])=[CH:19][CH:18]=1)[NH:6][C:7]1[CH:8]=[N:9][C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2.[OH-].[Na+]>CO.O1CCCC1>[F:29][C:2]([F:1])([F:28])[CH2:3][CH2:4][CH:5]([C:17]1[CH:18]=[CH:19][C:20]([C:21]([OH:23])=[O:22])=[CH:26][CH:27]=1)[NH:6][C:7]1[CH:8]=[N:9][C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86718839Ethyl (+/-)-4-(4,4,4-trifluoro-1-(quinolin-3-ylamino)butyl)benzoate

Product 1

HCID 86718840(+/-)-4-(4,4,4-Trifluoro-1-(quinolin-3-ylamino)butyl)benzoic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl(+/−)-4-(4,4,4-trifluoro-1-(quinolin-3-ylamino)butyl)benzoate (95 mg, 0.24 mmol) in methanol (1.2 mL) and tetrahydrofuran (1.2 mL) was added 1 N aq sodium hydroxide (1.2 mL, 1.2 mmol). After 17 hours, the solution was concentrated under reduced pressure to remove methanol and tetrahydrofuran. The mixture was then acidified to pH 5 with 1 N aq hydrochloric acid and diluted with sat. aq sodium chloride (20 mL). The mixture was extracted with ethyl acetate (3×20 mL). The combined organic layers were dried over Na2SO4 and filtered, and the filtrate was concentrated under reduced pressure to give (+/−)-4-(4,4,4-trifluoro-1-(quinolin-3-ylamino)butyl)benzoic acid. 1HNMR (400 MHz, CD3OD) δ 8.50 (br. s, 1H), 8.02 (d, J=8.2 Hz, 2H), 7.80-7.73 (m, 1H), 7.57 (d, J=8.2 Hz, 2H), 7.53-7.47 (m, 1H), 7.40-7.32 (m, 2H), 6.95 (d, J=2.5 Hz, 1H), 4.73-4.64 (m, 1H), 2.55-2.39 (m, 1H), 2.39-2.22 (m, 1H), 2.22-2.04 (m, 2H).

Workup

  1. concentrationthe solution was concentrated under reduced pressure
  2. customto remove methanol and tetrahydrofuran
  3. additiondiluted with sat. aq sodium chloride (20 mL)
  4. extractionThe mixture was extracted with ethyl acetate (3×20 mL)
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-03ef998b7ad44f9b8bd168074e0ff3e7
Source dataset
uspto-grants-2015_01
Patent number
US08927577B2

Reaction notes

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