Hydrochloric Acid → 7-Chloro-3-phenylcarbamoylmethyl-1,3,4,5-tetrahydrobenz[cd]indole-2-carboxylic acid

HRID 1439909Notes

Reaction equation

HRID 1439909 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](=[O:32])[NH:25][C:26]5[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=5)[C:12]([C:13]=34)=[C:11]2[C:33]([O:35]C)=[O:34])(=O)=O)C=CC=CC=1.CO.[OH-].[Na+].Cl>C1COCC1>[Cl:19][C:16]1[CH:15]=[C:14]2[CH2:20][CH2:21][CH:22]([CH2:23][C:24](=[O:32])[NH:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:12]3=[C:11]([C:33]([OH:35])=[O:34])[NH:10][C:18]([CH:17]=1)=[C:13]23

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 15337220Methyl 1-benzenesulfonyl-7-chloro-3-phenylcarbamoylmethyl-1,3,4,5-tetrahydrobenz[cd]indole-2-carboxylate

Product 1

HCID 108090767-Chloro-3-phenylcarbamoylmethyl-1,3,4,5-tetrahydrobenz[cd]indole-2-carboxylic acidYield 64.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 1-benzenesulfonyl-7-chloro-3-phenylcarbamoylmethyl-1,3,4,5-tetrahydrobenz[cd]indole-2-carboxylate (140 mg, 0.268 mmol) in a mixture of THF (3 mL), MeOH (3 mL), and 5N NaOH (3 mL) was stirred for 22 h at room temperature, acidified to pH 1 with 1N HCl, and, extracted with 1:1 THF/ethyl acetate. The organic layer was washed successively with water and brine, dried over magnesium sulfate, and concentrated. The residue was rinsed with dichloromethane and dried in vacuo to give 64 mg of the title compound (63%): 1H NMR (DMSO-d6) δ5 12.92 (bs, 1H), 11.44 (s, 1H), 9.86 (s, 1H), 7.60 (d, 2H, J=7.3 Hz), 7.30 (t, 2H, J=7.3 Hz), 7.16 (s, 1H), 7.03 (t, 1H, J=7.3 Hz), 6.85 (s, 1H), 3.89 (m, 1H), 3.06 (mt, 1H, J=12.6 Hz), 2.79 (md, 1H, J=16.8 Hz), 2.68 (dd, 1H, J=14.2, 4.3 Hz), 2.50 (m, 1H), 2.06 (md, 1H, J=12.2 Hz), 1.85 (m, 1H).

Workup

  1. extractionextracted with 1:1 THF/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 dichloromethane
  6. customdried in vacuo

Sources & evidence

ORD record
ord-6560003b03804aa3879aeb22fdaaaf91
Source dataset
uspto-grants-1996_03
Patent number
US05496843

Reaction notes

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