Hydrochloric Acid → HCID 44627932, compound

HRID 1817989Notes

Reaction equation

HRID 1817989 reaction equation
C[O:2][C:3](=[O:16])/[CH:4]=[CH:5]/[C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:14]=1[NH:13][CH:12]=[C:11]2[CH3:15].Cl>C1COCC1.CO.[OH-].[Na+]>[CH3:15][C:11]1[C:10]2[C:14](=[C:6](/[CH:5]=[CH:4]/[C:3]([OH:16])=[O:2])[CH:7]=[CH:8][CH:9]=2)[NH:13][CH:12]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 44627931HCID 44627931, compound

Product 1

HCID 44627932HCID 44627932, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

(I-7). To a solution of (E)-3-(3-methyl-1H-indol-7-yl)-acrylic acid methyl ester (2, 180 mg, 0.84 mmol) in THF (5 ml) and methanol (4 ml), NaOH aq. (4 ml) was added at rt. The reaction mixture was stirred at rt over night and then the pH was adjusted to acidic by adding aqueous 2N HCl. The reaction mixture was extracted with EtOAc (2×30 ml). The combined organic phases were washed with water, brine and dried over sodium sulfate. After removal of solvent, 170 mg of I-7 was obtained. 1H-NMR (500 MHz, DMSO-d6).

Workup

  1. extractionThe reaction mixture was extracted with EtOAc (2×30 ml)
  2. washThe combined organic phases were washed with water, brine
  3. dry with materialdried over sodium sulfate
  4. customAfter removal of solvent, 170 mg of
  5. customI-7 was obtained

Sources & evidence

ORD record
ord-6822edf6532146fca2463bcfe49b7115
Source dataset
uspto-grants-2009_10
Patent number
US07598397B2

Reaction notes

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