Chloroform → HCID 21527623, compound

HRID 1658485Notes

Reaction equation

HRID 1658485 reaction equation
[C:1]([NH:5][CH2:6][CH:7]([OH:20])[CH2:8][O:9][C:10]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:11]=1[CH2:12][C:13](=[O:19])[NH:14]2)([CH3:4])([CH3:3])[CH3:2].C(Cl)(Cl)Cl.[C:25](Cl)(=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[N:28][CH:27]=1>N1C=CC=CC=1>[C:1]([NH:5][CH2:6][CH:7]([O:20][C:25](=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[N:28][CH:27]=1)[CH2:8][O:9][C:10]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:11]=1[CH2:12][C:13](=[O:19])[NH:14]2)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6212ChloroformHCID 82604Nicotinoyl chlorideHCID 21527625HCID 21527625, compound

Product 1

HCID 21527623HCID 21527623, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1 g of 4-(3-tert-butylamino-2-hydroxypropoxy)oxindole, 20 cc of chloroform, 10 cc of pyridine and 0.713 g of nicotinoyl chloride are allowed to stand at room temperature for 4 days, the mixture is then concentrated by evaporation as carefully as possible at reduced pressure and the residue is taken up in water. The reaction mixture is rendered alkaline with a 10% ammonia solution, is extracted with methylene chloride, and subsequently an excess of 2 N hydrochloric acid in ethanol is added. The solvent and excess hydrochloric acid are carefully removed by evaporation at reduced pressure and the dihydrochloride of the title compound is crystallized from ethanol, needle druses. M.P. 215°-218° .

Workup

  1. concentrationthe mixture is then concentrated by evaporation as carefully as possible at reduced pressure
  2. extractionis extracted with methylene chloride
  3. additionsubsequently an excess of 2 N hydrochloric acid in ethanol is added
  4. customThe solvent and excess hydrochloric acid are carefully removed by evaporation at reduced pressure
  5. customthe dihydrochloride of the title compound is crystallized from ethanol, needle druses

Sources & evidence

ORD record
ord-f35ec86144bf441b9c6e923e6d3c09f2
Source dataset
uspto-grants-1976_06
Patent number
US03965095

Reaction notes

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