Hydrochloric Acid → 5-Chloro-2-methyl-3-phenylisoindole-1-carboxylic acid (4-oxopentyl)amide

HRID 1863092Notes

Reaction equation

HRID 1863092 reaction equation
[CH3:1][C:2]1([CH2:7][CH2:8][CH2:9][NH:10][C:11]([C:13]2[N:14]([CH3:29])[C:15]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[C:16]3[C:21]=2[CH:20]=[CH:19][C:18]([Cl:22])=[CH:17]3)=[O:12])OCC[O:3]1.O1CCOCC1.Cl>O>[O:3]=[C:2]([CH3:1])[CH2:7][CH2:8][CH2:9][NH:10][C:11]([C:13]1[N:14]([CH3:29])[C:15]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[C:16]2[C:21]=1[CH:20]=[CH:19][C:18]([Cl:22])=[CH:17]2)=[O:12]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 538171005-Chloro-2-methyl-3-phenylisoindole-1-carboxylic acid [3-(2-methyl-1,3-dioxolan-2-yl)-propyl]amide

Product 1

HCID 203933715-Chloro-2-methyl-3-phenylisoindole-1-carboxylic acid (4-oxopentyl)amide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A suspension of 8.3 g. of 5-chloro-2-methyl-3-phenylisoindole-1-carboxylic acid [3-(2-methyl-1,3-dioxolan-2-yl)propyl]amide in a mixture of 40 ml. of dioxane and 10 ml. of water is treated with 2 ml. of concentrated hydrochloric acid and then boiled at reflux for 3 hours. The solution obtained is concentrated to dryness under reduced pressure and the residue triturated with diethyl ether, and there is obtained 5-chloro-2-methyl-3-phenylisoindole-1-carboxylic acid (4-oxopentyl)amide having a melting point of 128°-131° C. which can be used in the process without further purification. An analytical sample is obtained by recrystallization from ethanol and has a melting point of 136°-138° C.

Workup

  1. additionA suspension of 8.3 g
  2. temperatureat reflux for 3 hours
  3. customThe solution obtained
  4. concentrationis concentrated to dryness under reduced pressure
  5. customthe residue triturated with diethyl ether

Sources & evidence

ORD record
ord-addfc1ad647844ab900dced71203f65b
Source dataset
uspto-grants-1979_09
Patent number
US04167632

Reaction notes

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