Methanol → 7-Chloro-3-carboxymethyl-1,3,4,5-tetrahydrobenz[cd]indole-2-carboxylic acid

HRID 1439906Notes

Reaction equation

HRID 1439906 reaction equation
C1(S([N:10]2[C:18]3[CH:17]=[C:16]([Cl:19])[CH:15]=[C:14]4[CH2:20][CH2:21][CH:22]([CH2:23][C:24]([OH:26])=[O:25])[C:12]([C:13]=34)=[C:11]2[C:27]([O:29]C)=[O:28])(=O)=O)C=CC=CC=1.CO.[OH-].[Na+].OS([O-])(=O)=O.[K+]>C1COCC1>[Cl:19][C:16]1[CH:15]=[C:14]2[CH2:20][CH2:21][CH:22]([CH2:23][C:24]([OH:26])=[O:25])[C:12]3=[C:11]([C:27]([OH:29])=[O:28])[NH:10][C:18]([CH:17]=1)=[C:13]23

Participants

6

Reactant 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 516920Potassium bisulfateHCID 15337219Methyl 1-benzenesulfonyl-7-chloro-3-carboxymethyl-1,3,4,5-tetrahydrobenz[cd]indole-2-carboxylate

Product 1

HCID 105178477-Chloro-3-carboxymethyl-1,3,4,5-tetrahydrobenz[cd]indole-2-carboxylic acidYield 58.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 1-benzenesulfonyl-7-chloro-3-carboxymethyl-1,3,4,5-tetrahydrobenz[cd]indole-2-carboxylate (143 mg, 0.328 mmol) in a mixture of THF (2 mL), MeOH (2 mL), and 5N NaOH (2 mL) was stirred for 19 h at room temperature, acidified to pH 3 with 5% KHSO4, and extracted with ethyl acetate. The organic layer was washed successively with water and brine, dried over magnesium sulfate, and concentrated. The residue was rinsed with dichloroethane and dried in vacuo to give 56 mg of the title compound (58%): 1H NMR (DMSO-d6) δ12.58 (bs, 1H), 11.45 (s, 1H), 7.14 (d, 1H, J=1.0 Hz), 6.83 (d, 1H, J=1.0 Hz), 3.76 (m, 1H), 2.93 (mt, 1H, J=12.7 Hz), 2.78 (md, 1H, J=15.8 Hz), 2.64 (dd, 1H, J=15.3, 3.0 Hz), 2.35 (dd, 1H, J=15.5, 11.5 Hz), 2.08 (md, 1H, J=12.2 Hz), 1.87 (m, 1H).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed successively with water and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. washThe residue was rinsed with dichloroethane
  6. customdried in vacuo

Sources & evidence

ORD record
ord-4638ced1f2eb47098c4fcb86d104f536
Source dataset
uspto-grants-1996_03
Patent number
US05496843

Reaction notes

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