Hydrochloric Acid → HCID 57303459, compound

HRID 2231978Notes

Reaction equation

HRID 2231978 reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.NCCNC(=O)[CH:15]([C:17]1[CH:22]=[C:21]([C:23]([CH3:26])([CH3:25])[CH3:24])[C:20]([OH:27])=[C:19]([C:28]([CH3:31])([CH3:30])[CH3:29])[CH:18]=1)[CH3:16].[N:33]1C2C(=CC=CC=2)C=CC=1.Cl.C[N:45]1[CH2:49][CH2:48]C[C:46]1=[O:50]>>[C:28]([C:19]1[CH:18]=[C:17]([CH2:15][CH2:16][C:46]([NH:45][CH2:49][CH2:48][NH:33][C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=2)=[O:50])[CH:22]=[C:21]([C:23]([CH3:26])([CH3:24])[CH3:25])[C:20]=1[OH:27])([CH3:31])([CH3:30])[CH3:29]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 7047QuinolineHCID 121634-ChlorobenzonitrileHCID 13387N-methyl-2-pyrrolidoneHCID 22104623HCID 22104623, compound

Product 1

HCID 57303459HCID 57303459, compound

Procedure

13.75 g of 4-chlorobenzonitrile and 32 g of 3,5-di-tert-butyl-4-hydroxyphenylpropionic acid 2-aminoethylamide are reacted with 12.9 g of quinoline in 0.2 l of N-methylpyrrolidone at 180° C. for 8 hours, after which the mixture is cooled, stirred into 0.5 l of 7% strength hydrochloric acid and extracted with 0.2 l of toluene, the toluene extract is evaporated down and the residue is purified over a silica gel column (mobile phase: ethyl acetate). The product has a melting point of 146°-148° C.

Workup

  1. temperatureafter which the mixture is cooled
  2. extractionextracted with 0.2 l of toluene
  3. extractionthe toluene extract
  4. customis evaporated down
  5. customthe residue is purified over a silica gel column (mobile phase: ethyl acetate)

Sources & evidence

ORD record
ord-d7157ad74467489499b9cd605159089c
Source dataset
uspto-grants-1988_11
Patent number
US04785107

Reaction notes

Loading…