Methyl 2-formylbenzoate → HCID 69235964, compound

HRID 878795Notes

Reaction equation

HRID 878795 reaction equation
[CH:1]([NH:4][S:5]([C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12](=[O:17])[CH2:11]2)(=[O:7])=[O:6])([CH3:3])[CH3:2].[CH:18]([C:20]1[CH:29]=[CH:28][CH:27]=[CH:26][C:21]=1[C:22]([O:24][CH3:25])=[O:23])=O.CCCCCC.C(OCC)(=O)C>C(O)C.N1CCCCC1>[CH3:25][O:24][C:22](=[O:23])[C:21]1[CH:26]=[CH:27][CH:28]=[CH:29][C:20]=1[CH:18]=[C:11]1[C:10]2[C:14](=[CH:15][CH:16]=[C:8]([S:5](=[O:7])(=[O:6])[NH:4][CH:1]([CH3:3])[CH3:2])[CH:9]=2)[NH:13][C:12]1=[O:17]

Participants

6

Reactant 3

HCID 243003Methyl 2-formylbenzoateHCID 21226206Ethyl acetate hexaneHCID 219156105-Isopropylaminosulfonyl-2-oxindole

Product 1

HCID 69235964HCID 69235964, compound

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 702EthanolSolvent

Procedure

A solution of rpm281 (0.149 g, 0.586 mmol) and methyl 2-formylbenzoate (0.105 g, 0.645 mmol, 1.1 eq) in ethanol (10 ml) was stirred in presence of piperidine (1 drop) at 80° C., under Ar for 1 h. After cooling to room temperature, the solvent was removed under reduced pressure. The residue was dissolved in ethyl acetate (15 ml) and washed with HCl 1M (10 ml). The organic extracts were collected, dried over Na2SO4 and the solvent removed under reduced pressure to afford a orange solid. The pure compound rpm347 was obtained after trituration with hexane/ethyl acetate mixture (6:4) (10 ml) as a off-white solid (0.135 g, 0.337 mmol, 60%), mp 271-273° C. MS (API-ES): m/z 401 (M+H)+; HRMS (API-ES) m/z Found: 401.1173 (M+H)+.

Workup

  1. customthe solvent was removed under reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate (15 ml)
  3. washwashed with HCl 1M (10 ml)
  4. customThe organic extracts were collected
  5. dry with materialdried over Na2SO4
  6. customthe solvent removed under reduced pressure
  7. customto afford a orange solid

Sources & evidence

ORD record
ord-f42f52da530e4a36945aee2f09a4a077
Source dataset
uspto-grants-2015_03
Patent number
US08987474B2

Reaction notes

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