p-Toluenesulfonic acid → HCID 15337218, compound

HRID 1439922Notes

Reaction equation

HRID 1439922 reaction equation
[CH3:1][O:2][C:3]([C:5]1[NH:6][C:7]2[CH:8]=[C:9]([Cl:25])[CH:10]=[C:11]3[CH2:16][CH2:15][CH:14]([CH2:17][C:18]([O:20]C(C)(C)C)=[O:19])[C:13]=1[C:12]=23)=[O:4].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH3:1][O:2][C:3]([C:5]1[NH:6][C:7]2[CH:8]=[C:9]([Cl:25])[CH:10]=[C:11]3[CH2:16][CH2:15][CH:14]([CH2:17][C:18]([OH:20])=[O:19])[C:13]=1[C:12]=23)=[O:4]

Participants

5

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 15337217HCID 15337217, compound

Product 1

HCID 15337218HCID 15337218, compoundYield 114.2%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 7-chloro-3-tert-butoxycarbonylmethyl-1,3,4,5-tetrahydrobenz[cd]indole-2-carboxylic acid methyl ester (54 mg, 0.148 mmol) and p-toluenesulfonic acid (3 mg) in toluene (1 mL) was refluxed for 1 h, diluted with ethyl acetate, washed with water and brine, dried over MgSO4, and concentrated to give 52 mg of the title compound (quant): 1H NMR (DMSO-d6) δ12.17 (bs, 1H), 11.60 (s, 1H), 7.17 (s, 1H), 6.84 (s, 1H), 3.88 (s, 3H), 3.77 (m, 1H), 2.94 (mt, 1H, J=13.9 Hz), 2.80 (md, 1H, J=17.2 Hz), 2.56 (dd, 1H, J=15.2, 4.3 Hz), 2.37 (dd, 1H, J=15.2, 10.6 Hz), 2.11 (md, 1H, J=12.5 Hz), 1.88 (m, H).

Workup

  1. temperaturewas refluxed for 1 h
  2. washwashed with water and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e3a0c070ff2447b4a5e5a627617e120f
Source dataset
uspto-grants-1996_03
Patent number
US05496843

Reaction notes

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