Ammonium Chloride → HCID 23156849, compound

HRID 1162900Notes

Reaction equation

HRID 1162900 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:13])=[C:6]([CH:12]=1)[C:7]([N:9]([CH3:11])C)=[O:8].[CH2:14]1[N:19]([C:20]2[C:25](C#N)=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:18][CH2:17][O:16][CH2:15]1.[Cl-].[NH4+]>C1COCC1>[Cl:1][C:2]1[CH:12]=[C:6]2[C:5]([CH:13]=[C:11]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=3[N:19]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)[NH:9][C:7]2=[O:8])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 27370122-MorpholinobenzonitrileHCID 14839220HCID 14839220, compound

Product 1

HCID 23156849HCID 23156849, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-78 °C

Procedure

A 1.8 M lithium diisopropylamide THF solution (5.39 ml, 9.69 mmol) was diluted with THF (10 ml). To the diluted solution, a solution obtained by dissolving the 5-chloro-2,N,N-trimethylbenzamide (383 mg, 1.94 mmol) prepared in step A in THF (5 ml) was added dropwise at −78° C. A solution obtained by dissolving 2-(4-morpholino)benzonitrile (438 mg, 2.33 mmol) in THF (5 ml) was further added to the mixture. The obtained mixture was stirred at −78° C. for 30 minutes. Thereafter, a saturated ammonium chloride aqueous solution was added to the reaction solution, followed by extraction with ethyl acetate. The extract was washed with a saturated saline solution, and was then dried over anhydrous sodium sulfate, followed by concentration under reduced pressure. The obtained yellow oil product was crystallized from hexane/ethyl acetate (3:1), so as to obtain 7-chloro-3-(2-morpholin-4-ylphenyl)-2H-isoquinolin-1-one (575 mg; yield: 87%) in the form of a colorless crystal.

Workup

  1. customTo the diluted solution, a solution obtained
  2. additionwas added dropwise at −78° C
  3. customA solution obtained
  4. additionwas further added to the mixture
  5. extractionfollowed by extraction with ethyl acetate
  6. washThe extract was washed with a saturated saline solution
  7. dry with materialwas then dried over anhydrous sodium sulfate
  8. concentrationfollowed by concentration under reduced pressure
  9. customThe obtained yellow oil product was crystallized from hexane/ethyl acetate (3:1)

Sources & evidence

ORD record
ord-72dda3fdf02344b28f5e42c4f5a3e8b5
Source dataset
uspto-grants-2010_10
Patent number
US07820693B2

Reaction notes

Loading…