Ammonia → 3-Amino-3-(2-ethoxy-phenyl)-5-methoxy-1,3-dihydro-indol-2-one

HRID 601776Notes

Reaction equation

HRID 601776 reaction equation
Cl[C:2]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[O:20][CH2:21][CH3:22])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:11][CH3:12])[CH:9]=2)[NH:4][C:3]1=[O:13].[NH3:23]>C(Cl)Cl.C(O)C>[NH2:23][C:2]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[O:20][CH2:21][CH3:22])[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([O:11][CH3:12])[CH:9]=2)[NH:4][C:3]1=[O:13]

Participants

5

Reactant 2

HCID 222AmmoniaHCID 575177773-Chloro-3-(2-ethoxy-phenyl)-5-methoxy-1,3-dihydro-indol-2-one

Product 1

HCID 575177783-Amino-3-(2-ethoxy-phenyl)-5-methoxy-1,3-dihydro-indol-2-one

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

3.2 g (10 mmol) of the intermediate from step B were suspended in 40 ml CH2Cl2. 50 ml of a 2M solution of NH3 in ethanol were added and the reaction mixture was stirred for 16 h at ambient temperature. The mixture was poured into an ice/water mixture and the precipitate was separated. The precipitate was redissolved in ethyl acetate. This organic phase was washed with 2M aqueous HCl. The aqueous phase was made alkaline (pH=8-9) and then extracted with ethyl acetate. The organic phase was dried over magnesium sulfate and the solvent was removed in vacuo to yield 1.7 g of the intermediate.

Workup

  1. customthe precipitate was separated
  2. dissolutionThe precipitate was redissolved in ethyl acetate
  3. washThis organic phase was washed with 2M aqueous HCl
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic phase was dried over magnesium sulfate
  6. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-60f02df553c84cccbba38c00638ba906
Source dataset
uspto-grants-2011_03
Patent number
US07902379B2

Reaction notes

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