Ammonia → HCID 178513667, compound

HRID 24750Notes

Reaction equation

HRID 24750 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10]/[C:11](=[C:18]2\[C:19](=[O:27])[NH:20][C:21]3[C:26]\2=[CH:25][CH:24]=[CH:23][CH:22]=3)/[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:6][CH:5]=1)([OH:3])=O.C1N=C[N:30](C(N2C=NC=C2)=O)C=1.N.O>CN(C=O)C>[NH2:30][C:1]([C:4]1[CH:5]=[CH:6][C:7]([NH:10]/[C:11](=[C:18]2\[C:19](=[O:27])[NH:20][C:21]3[C:26]\2=[CH:25][CH:24]=[CH:23][CH:22]=3)/[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[CH:8][CH:9]=1)=[O:3]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 962WaterHCID 682631,1'-CarbonyldiimidazoleHCID 1785170884-[[(Z)-(2-oxo-1H-indol-3-ylidene)-phenylmethyl]amino]benzoic acid

Product 1

HCID 178513667HCID 178513667, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

356 mg (1 mmol) of (Z)-3-[1-(4-carboxyphenylamino)-1-phenyl-methylidene]-2-indolinone are dissolved in 10 ml of DMF and combined with 194 mg (1 mmol) of CDI. The mixture is stirred for 2 hours at ambient temperature, 2 ml of methanolic ammonia solution are added, then stirring is continued for 16 hours at ambient temperature. Then water is added, the precipitate is removed by suction filtering, washed with water and a little ether and dried at 80° C.

Workup

  1. stirringstirring
  2. waitis continued for 16 hours at ambient temperature
  3. customthe precipitate is removed by suction
  4. filtrationfiltering
  5. washwashed with water
  6. dry with materiala little ether and dried at 80° C.

Sources & evidence

ORD record
ord-f1a2852f5e9f4edd96547e2fcefc79a7
Source dataset
uspto-grants-2005_02
Patent number
US06855710B2

Reaction notes

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