Hydrochloric Acid → 3-(6-methyl-1H-indol-2-yl)propanoic acid

HRID 589604Notes

Reaction equation

HRID 589604 reaction equation
[CH3:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([CH2:11][CH2:12][C:13]([O:15]C)=[O:14])[NH:8]2)=[CH:4][CH:3]=1.O[Li].O.Cl>C1COCC1.CO.O.O>[CH3:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[C:7]([CH2:11][CH2:12][C:13]([OH:15])=[O:14])[NH:8]2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 71625638methyl 3-(6-methyl-1H-indol-2-yl)propanoate

Product 1

HCID 826084063-(6-methyl-1H-indol-2-yl)propanoic acidYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To a solution of 46 (0.69 g, 3.17 mmol) in THF:MeOH:H2O (1:1:1) (9 mL) was added LiOH.H2O (0.25 g, 5.96 mmol). The reaction was stirred at rt for 16 h, diluted with water, acidified to pH 3 with 1 N HCl, and extracted with EtOAc. The combined organic layers were washed with water, brine, dried over MgSO4, and concentrated in vacuo to provide 0.58 g (90%) of product 47 as an off-white solid. 1H NMR (300 MHz, DMSO-d6) δ 2.35 (s, 3H), 2.65 (t, J=8 Hz, 2H), 2.93 (t, J=8 Hz, 2H), 6.05 (s, 1H), 6.75 (d, J=8 Hz, 1H), 7.04 (s, 1H), 7.27 (d, J=8 Hz, 1H), 10.74 (brs, 1H), 12.19 (brs, 1H). LC-MS (CI): m/z 202.0 [(M−H)− C12H13NO2 requires 203.09].

Workup

  1. extractionextracted with EtOAc
  2. washThe combined organic layers were washed with water, brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6443e39423a048889c05f6b6020639f4
Source dataset
uspto-grants-2016_01
Patent number
US09233921B2

Reaction notes

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