Sodium Hydroxide → 4-[3-Methyl-1-(8-methyl-quinolin-3-ylamino)-butyl]benzoic acid

HRID 1424277Notes

Reaction equation

HRID 1424277 reaction equation
C([O:3][C:4](=[O:28])[C:5]1[CH:10]=[CH:9][C:8]([CH:11]([NH:16][C:17]2[CH:18]=[N:19][C:20]3[C:25]([CH:26]=2)=[CH:24][CH:23]=[C:22](C)[CH:21]=3)[CH2:12][CH:13]([CH3:15])[CH3:14])=[CH:7][CH:6]=1)C.[OH-].[Na+].[CH2:31]1COCC1.CO>>[CH3:15][CH:13]([CH3:14])[CH2:12][CH:11]([C:8]1[CH:9]=[CH:10][C:5]([C:4]([OH:3])=[O:28])=[CH:6][CH:7]=1)[NH:16][C:17]1[CH:18]=[N:19][C:20]2[C:25]([CH:26]=1)=[CH:24][CH:23]=[CH:22][C:21]=2[CH3:31]

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 21899815MeOH tetrahydrofuranHCID 712393454-[3-Methyl-1-(7-methyl-quinoline-3-ylamino)-butyl]-benzoic acid ethyl ester

Product 1

HCID 712394574-[3-Methyl-1-(8-methyl-quinolin-3-ylamino)-butyl]benzoic acidYield 100%

Procedure

A mixture of 4-[3-Methyl-1-(7-methyl-quinoline-3-ylamino)-butyl]-benzoic acid ethyl ester (48 mg, 0.13 mM) and 1N aqueous NaOH solution (0.318 mL, 0.318 mM) in THF-MeOH (1:1, 1.5 mL) was heated to 50° for 5 h. The reaction was cooled, concentrated to remove organic solvent. The aqueous solution was diluted with DCM (5 mL), acidified by 1N HCl solution to pH=3-4. The organic solution was separated and the aqueous solution was extracted with DCM (3×5 mL). The combined organic solution were dried (Na2SO4) and concentrated to give a yellow solid product (44 mg, −100%). 1H NMR (400 MHz, CD3OD) δ ppm 0.97 (d, J=6.44 Hz, 3H) 1.02 (d, J=6.44 Hz, 3H) 1.54-1.67 (m, 1H) 1.73-1.91 (m, 2H) 2.43 (s, 3H) 4.57-4.65 (m, 1H) 7.14 (d, J=2.54 Hz, 1H) 7.28 (dd, J=8.49, 1.27 Hz, 1H) 7.46-7.58 (m, 4H) 7.97 (d, 2H) 8.44 (d, J=2.34 Hz, 1H), two protons (COOH and NH) were exchanged. LC-MS: m/z 349.1 (M+1). This material will be used for the next step reaction without further work-up.

Workup

  1. temperaturewas heated to 50° for 5 h
  2. temperatureThe reaction was cooled
  3. concentrationconcentrated
  4. customto remove organic solvent
  5. additionThe aqueous solution was diluted with DCM (5 mL)
  6. customThe organic solution was separated
  7. extractionthe aqueous solution was extracted with DCM (3×5 mL)
  8. dry with materialThe combined organic solution were dried (Na2SO4)
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-c041580f6dc4415ab88b6c6b177787d4
Source dataset
uspto-grants-2015_01
Patent number
US08927577B2

Reaction notes

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