Water → Carbonic acid-[5-chloro-2-oxo-3-(2-methoxy-phenyl)-2,3-dihydro-1-H-indole-3-yl] ester phenyl-amide

HRID 552306Notes

Reaction equation

HRID 552306 reaction equation
C([O:3][C:4](Cl)=[O:5])C.N[C:8]1([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[O:25][CH3:26])[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([Cl:17])[CH:15]=2)[NH:10][C:9]1=[O:18].[OH2:27]>N1C=CC=CC=1.CCOCC>[Cl:17][C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9](=[O:18])[C:8]2([O:3][C:4](=[O:5])[OH:27])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[O:25][CH3:26].[C:11]1([NH-:10])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 962WaterHCID 10928Ethyl chloroformateHCID 219254143-Amino-5-chloro-1,3-dihydro-3-(2-methoxyphenyl)indol-2-one

Product 1

HCID 86625959Carbonic acid-[5-chloro-2-oxo-3-(2-methoxy-phenyl)-2,3-dihydro-1-H-indole-3-yl] ester phenyl-amide

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 3283Diethyl EtherSolvent

Procedure

0.38 ml (3.1 mmol) chloroformic acid ethyl ester were added to 0.8 g (2.8 mmol) of the intermediate product 3b in 20 ml pyridine at 0° C., and then everything was stirred for 16 h at room temperature. Then the batch was poured on to icy water and extracted with ethyl acetate. The organic phase was washed with water, dried and concentrated in a vacuum. The residue obtained in this way was dissolved in a little ether and the product was precipitated by the careful addition of n-pentane. 1.1 g were obtained.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase was washed with water
  3. customdried
  4. concentrationconcentrated in a vacuum
  5. customThe residue obtained in this way
  6. customthe product was precipitated by the careful addition of n-pentane
  7. custom1.1 g were obtained

Sources & evidence

ORD record
ord-26f92144996a42f5a42cd5ae34c724f2
Source dataset
uspto-grants-2011_05
Patent number
US07951807B2

Reaction notes

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