Quinoline → Isoquinoline

HRID 259079

Reaction equation

HRID 259079 reaction equation
CC(OCC1CS[C@@H]2[C@H](NC(CCC[C@@H](N)C(O)=O)=O)C(=O)N2C=1C(O)=O)=O.[N:29]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:32]=[CH:31][CH:30]=1>[Cl-].[Na+]>[CH:38]1[C:33]2[C:32](=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:31]=[CH:30][N:29]=1

Participants

4

Reactant 2

HCID 7047QuinolineHCID 65536Cephalosporin C

Product 1

HCID 8405Isoquinoline

Reagents, catalysts & solvents 1

HCID 5234Sodium ChlorideSolvent

Procedure

15 ml of the remaining reaction solution were diluted with 5% sodium chloride solution to make 30 ml (corresponds to 0.5% solution calculated as cephalosporin C). After adding 0.22 ml of quinoline to the solution, the mixture was adjusted to pH 3.0 and stirred at 5 - 10° C. Very soon crystals are separated out. The crystals were collected after an hour, washed with ice-water and with ethyl acetate and dried in vacuo. 226 mg of isoquinoline adduct of N-methylthioacetyl-cephalosporin C having 97% purity were obtained.

Workup

  1. custom15 ml of the remaining reaction solution
  2. customVery soon crystals are separated out
  3. customThe crystals were collected after an hour
  4. washwashed with ice-water and with ethyl acetate
  5. customdried in vacuo

Sources & evidence

ORD record
ord-c9cb96fd44074840bf3b3fb02d3679d6
Source dataset
uspto-grants-1977_07
Patent number
US04036833

Linked notes

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