Sodium Hydroxide → 2-(1,2,3,4-Tetrahydro-2,6-dimethylpyrido[3,4-b]indol-9-yl)acetic acid

HRID 2198347Notes

Reaction equation

HRID 2198347 reaction equation
[CH3:1][N:2]1[CH2:14][CH2:13][C:12]2[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([CH3:15])[CH:10]=3)[N:5]([CH2:16][C:17]([O:19]CC)=[O:18])[C:4]=2[CH2:3]1.[OH-].[Na+]>C1COCC1.O>[CH3:1][N:2]1[CH2:14][CH2:13][C:12]2[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([CH3:15])[CH:10]=3)[N:5]([CH2:16][C:17]([OH:19])=[O:18])[C:4]=2[CH2:3]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 57930374Ethyl 2-(1,2,3,4-tetrahydro-2,6-dimethylpyrido[3,4-b]indol-9-yl)acetate

Product 1

HCID 442426452-(1,2,3,4-Tetrahydro-2,6-dimethylpyrido[3,4-b]indol-9-yl)acetic acidYield 21%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
75 °C

Procedure

Ethyl 2-(1,2,3,4-tetrahydro-2,6-dimethylpyrido[3,4-b]indol-9-yl)acetate (0.35 g, 1.2 mmol) in THF (10 mL) was added to a solution of sodium hydroxide (0.146 g, 3.6 mmol) in water (3 mL) and heated at 75° C. for 1 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the solvent was removed; water (10 mL) was added to the residue and the aqueous layer was washed with ethyl acetate (2×10 mL). The pH of aqueous layer was adjusted to 2-3, and the aqueous layer was washed with ethyl acetate. The aqueous layer was evaporated, the residue was extracted with methanol, filtered, the filtrate was concentrated under reduced pressure to yield 2-(1,2,3,4-tetrahydro-2,6-dimethylpyrido[3,4-b]indol-9-yl)acetic acid (65 mg). 1H NMR (CD3OD): 7.30 (s, 1H) 7.20 (d, 1H), 7.0 (d, 1H), 5.1 (d, 1H), 4.8 (d, 1H), 4.18 (m, 1H), 4.0 (s, 2H), 3.81 (m, 1H), 3.42 (s, 3H), 3.15 (bs, 2H), 2.4 (s, 3H).

Workup

  1. customAfter completion of the reaction
  2. customthe solvent was removed
  3. additionwater (10 mL) was added to the residue
  4. washthe aqueous layer was washed with ethyl acetate (2×10 mL)
  5. washthe aqueous layer was washed with ethyl acetate
  6. customThe aqueous layer was evaporated
  7. extractionthe residue was extracted with methanol
  8. filtrationfiltered
  9. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c8780f0c1c2f4f2e8f3d34d73efc10a1
Source dataset
uspto-grants-2012_12
Patent number
US08338447B2

Reaction notes

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