Methanesulfonic Acid → HCID 178497643, compound

HRID 878793Notes

Reaction equation

HRID 878793 reaction equation
C[N:2]([CH:4]=[C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([S:14]([OH:17])(=[O:16])=O)[CH:12]=2)[NH:7][C:6]1=[O:18])[CH3:3].[CH3:19][O:20][C:21](=[O:29])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24]C=1N.CS(O)(=O)=O>C(O)C>[CH3:19][O:20][C:21](=[O:29])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:3]=1[NH:2][CH:4]=[C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([S:14](=[O:16])(=[O:17])[NH:7][CH:8]([CH3:13])[CH3:9])[CH:12]=2)[NH:7][C:6]1=[O:18]

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 8635Methyl AnthranilateHCID 909680093-Dimethylaminomethylene-2-oxo-2,3-dihydro-1h-indole-5-sulfonic acid

Product 1

HCID 178497643HCID 178497643, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of rpm282 (0.260 g, 0.841 mmol) methyl-2-aminobenzoate (0.139 g, 0.925 mmol, 1.2 eq) and methansulfonic acid (0.088 g, 0.925 mmol, 1.1 eq) in ethanol (5 mL) was heated in the microwave at 150° C. for 5 min. The reaction mixture was cooled to 0° C., and the orange precipitate was collected by filtration and dried, to give pure rpm335 (0.207 g, 0.498 mmol, 59%). MS (API-ES): m/z 416 (M+H)+; HRMS (API-ES) m/z Found: 416.1276 (M+H)+.

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. filtrationthe orange precipitate was collected by filtration
  3. customdried
  4. customto give pure rpm335 (0.207 g, 0.498 mmol, 59%)

Sources & evidence

ORD record
ord-ccc7760a6fa74402bce7641f85dbf4a8
Source dataset
uspto-grants-2015_03
Patent number
US08987474B2

Reaction notes

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