Sodium Hydroxide → HCID 69673878, compound

HRID 2276355Notes

Reaction equation

HRID 2276355 reaction equation
C([O:3][C:4](=[O:33])[CH:5]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[C:6]1[C:7]([CH3:27])=[N:8][C:9]2[C:14]([C:15]=1[C:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=1)=[CH:13][C:12]1[CH2:23][CH2:24][CH2:25][CH2:26][C:11]=1[CH:10]=2)C.[OH-].[Na+]>C(O)C.O1CCCC1>[C:29]([O:28][CH:5]([C:6]1[C:7]([CH3:27])=[N:8][C:9]2[C:14]([C:15]=1[C:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=1)=[CH:13][C:12]1[CH2:23][CH2:24][CH2:25][CH2:26][C:11]=1[CH:10]=2)[C:4]([OH:33])=[O:3])([CH3:32])([CH3:31])[CH3:30]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 67618881HCID 67618881, compound

Product 1

HCID 69673878HCID 69673878, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A 50 mL flask containing a solution of tert-butoxy-(2-methyl-4-p-tolyl-6,7,8,9-tetrahydro-benzo[g]quinolin-3-yl)-acetic acid ethyl ester (11.1 mg 25.0 μmol) in ethanol (1 mL) and tetrahydrofuran (1 mL) under nitrogen was added sodium hydroxide solution (1.0 M, 250 μL, 250 μmol) and stirred at ambient temperature overnight. Complete conversion was then achieved by heating to 60 C for 30 min. Evaporated in vacuo and azeotroped with toluene (2×5 mL). Residue was taken up in water (10 mL) and acidified to pH=2 with hydrochloric acid solution (2 M) then extracted into ethyl acetate (2×10 mL). Organics were dried with magnesium sulfate and evaporated onto silica gel. Chromatographed using ISCO Companion with a Redisep silica gel 4 g cartridge with an isocratic gradient of ethyl acetate:acetic acid (90:10). Evaporation gave tert-butoxy-(2-methyl-4-p-tolyl-6,7,8,9-tetrahydro-benzo[g]quinolin-3-yl)-acetic acid as a colorless solid 7.1 mg (68% Yield). LCMS (12 min acidic) 5.32 min 100% pure by ELSD and UV AP+ and ES+ 418. HNMR (CDCl3) >95% pure 7.77 (br-s, 1H), 7.59 (br-d, 1H), 7.36-7.32 (br-m, 2H), 7.22 (br-d, 1H), 7.10 (br-s, 1H), 5.29 (br-s, 1H), 2.99 (br-t, 2H), 2.85-2.78 (m, 4H), 2.49 (s, 3H), 2.18 (s, 3H), 1.86-1.81 (m, 4H), 0.98 (s, 9H)

Workup

  1. temperatureby heating to 60 C for 30 min
  2. customEvaporated in vacuo
  3. customazeotroped with toluene (2×5 mL)
  4. extractionthen extracted into ethyl acetate (2×10 mL)
  5. dry with materialOrganics were dried with magnesium sulfate
  6. customevaporated onto silica gel
  7. customChromatographed
  8. customEvaporation

Sources & evidence

ORD record
ord-7231b39bc18d4427938e18c4d0837e40
Source dataset
uspto-grants-2015_09
Patent number
US09132129B2

Reaction notes

Loading…