2-Methylbenzenesulfonic acid hydrate → methyl 1-(4-aminosulfonylphenyl)methylene-5-methoxy-2-methyl-1H-3-indenylacetate

HRID 542226Notes

Reaction equation

HRID 542226 reaction equation
[NH2:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]=[C:12]2[C:20]3[C:15](=[CH:16][C:17]([O:21][CH3:22])=[CH:18][CH:19]=3)[C:14]([CH2:23][C:24]([OH:26])=[O:25])=[C:13]2[CH3:27])=[CH:7][CH:6]=1)(=[O:4])=[O:3].O.[C:29]1(C)C(S(O)(=O)=O)=CC=CC=1>CO>[NH2:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([CH:11]=[C:12]2[C:20]3[C:15](=[CH:16][C:17]([O:21][CH3:22])=[CH:18][CH:19]=3)[C:14]([CH2:23][C:24]([O:26][CH3:29])=[O:25])=[C:13]2[CH3:27])=[CH:9][CH:10]=1)(=[O:3])=[O:4]

Participants

4

Reactant 2

HCID 124969952-Methylbenzenesulfonic acid hydrateHCID 676380441-(4-aminosulfonylphenyl)methylene-5-methoxy-2-methyl-1H-3-indenyl acetic acid

Product 1

HCID 70401818methyl 1-(4-aminosulfonylphenyl)methylene-5-methoxy-2-methyl-1H-3-indenylacetateYield 202.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of the E acid 3a (950 mg) and toluenesulfonic acid monohydrate (200 mg) in methanol (60 ml) was refluxed for 1-2 hours. The solution was filtered and the filtrate was concentrated to 30 ml. After cooling at 0° to 5° for 1 hour, the crystals were collected and dried. The crude ester was recrystallized from acetonitrile to give the pure E methyl 1-(4-aminosulfonylphenyl)methylene-5-methoxy-2-methyl-1H-3-indenylacetate 5a (850 mg, 86%): m.p. 169.5°-171.0° C.

Workup

  1. filtrationThe solution was filtered
  2. concentrationthe filtrate was concentrated to 30 ml
  3. temperatureAfter cooling at 0° to 5° for 1 hour
  4. customthe crystals were collected
  5. customdried
  6. customThe crude ester was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-da65aaf62ed549a8a03399190e3360e3
Source dataset
uspto-grants-1987_04
Patent number
US04656190

Reaction notes

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