Hydrochloric Acid → HCID 86645383, compound

HRID 222547Notes

Reaction equation

HRID 222547 reaction equation
C([O-])([O-])=O.[K+].[K+].[C:7]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[NH:16][C:17](=O)[CH2:18][N:19]1[C:27](=[O:28])[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:20]1=[O:29])(=O)[CH3:8].Cl.O=P(Cl)(Cl)[Cl:34]>CN(C=O)C.C1(C)C=CC=CC=1>[Cl:34][C:17]1[C:18]([N:19]2[C:27](=[O:28])[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:20]2=[O:29])=[C:7]([CH3:8])[C:10]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:16]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 24813Phosphorus oxychlorideHCID 8749607HCID 8749607, compound

Product 1

HCID 86645383HCID 86645383, compoundYield 79.7%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

1.4 g (10.4 mmol) of K2CO3 were added to a solution of 2.7 g (6.9 mmol) of N-(2-acetylphenyl)-2-(1,3-dioxoisoindolin-2-yl)-acetamide in DMF (27 ml), and the mixture was heated for 16 h at 60° C. After cooling to RT, the pH was adjusted to 2-3 with 2N hydrochloric acid. The resulting precipitate was filtered off with suction and dried in vacuo at 70° C. 9 ml (97 mmol) of POCl3 were added to the residue. This solution was heated for 2 h at 100° C. and then stirred for 16 h at RT. Toluene was then added and concentration was carried out in vacuo. This procedure was repeated, there being obtained as residue 2.13 g (5.5 mmol, 79%) of 2-(2-chloro-4-methylquinolin-3-yl)isoindoline-1,3-dione, which was reacted further without additional purification.

Workup

  1. temperatureAfter cooling to RT
  2. filtrationThe resulting precipitate was filtered off with suction
  3. customdried in vacuo at 70° C
  4. temperatureThis solution was heated for 2 h at 100° C.
  5. concentrationconcentration

Sources & evidence

ORD record
ord-1c07a7ff92fb4d518fa02312faae9ada
Source dataset
uspto-grants-2012_06
Patent number
US08207342B2

Reaction notes

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