Hydrochloric Acid → 7,7-Dimethyl-5,6,7,8-tetrahydro-quinoline-2-carboxylic acid

HRID 927574Notes

Reaction equation

HRID 927574 reaction equation
C[O:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]2[CH2:11][CH2:10][C:9]([CH3:16])([CH3:15])[CH2:8][C:7]=2[N:6]=1)=[O:4].O.[OH-].[Li+].Cl>C1COCC1.O>[CH3:15][C:9]1([CH3:16])[CH2:8][C:7]2[N:6]=[C:5]([C:3]([OH:4])=[O:2])[CH:14]=[CH:13][C:12]=2[CH2:11][CH2:10]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 710873877,7-Dimethyl-5,6,7,8-tetrahydro-quinoline-2-carboxylic acid methyl ester

Product 1

HCID 710874727,7-Dimethyl-5,6,7,8-tetrahydro-quinoline-2-carboxylic acidYield 96.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

7,7-Dimethyl-5,6,7,8-tetrahydro-quinoline-2-carboxylic acid methyl ester (1.88 g, 8.57 mmol) was dissolved in THF (30 mL) and water (10 mL). Lithium hydroxide monohydrate (616 mg, 25.7 mmol) was added with stirring at room temperature and the reaction mixture was stirred at reflux temperature for 1 h. The mixture was cooled, acidified with 2 N HCl to pH=5 and extracted with ethyl acetate. The organic phases were combined, dried with Na2SO4, and concentrated in vacuo. The residue was stirred with ethyl acetate (5 mL) at 40° C.; n-heptane (10 mL) was added and stirring at room temperature continued for 30 min. The precipitate was filtered and dried to give 1.7 g (96%) of the title compound as white solid; MS (ISP): m/e 206.1 [M+H]+.

Workup

  1. stirringthe reaction mixture was stirred
  2. temperatureat reflux temperature for 1 h
  3. temperatureThe mixture was cooled
  4. extractionextracted with ethyl acetate
  5. dry with materialdried with Na2SO4
  6. concentrationconcentrated in vacuo
  7. stirringThe residue was stirred with ethyl acetate (5 mL) at 40° C.
  8. additionn-heptane (10 mL) was added
  9. stirringstirring at room temperature
  10. filtrationThe precipitate was filtered
  11. customdried

Sources & evidence

ORD record
ord-3c99bef482284374a4adfb58df853d6b
Source dataset
uspto-grants-2016_03
Patent number
US09290451B2

Reaction notes

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