Ammonium Chloride → HCID 21496693, compound

HRID 1730245Notes

Reaction equation

HRID 1730245 reaction equation
[CH3:1][Mg]Cl.[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:19](=[O:20])[C:18]3[CH2:17][CH2:16][CH2:15][CH2:14][C:13]=3[C:12]2=[O:21])=[C:7]([F:22])[CH:6]=1.[Cl-].[NH4+]>O1CCCC1>[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:12]([OH:21])([CH3:1])[C:13]3[CH2:14][CH2:15][CH2:16][CH2:17][C:18]=3[C:19]2=[O:20])=[C:7]([F:22])[CH:6]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 1859312-(4-Chloro-2-fluorophenyl)-4,5,6,7-tetrahydro-1h-isoindole-1,3(2h)-dioneHCID 178418332HCID 178418332, compound

Product 1

HCID 21496693HCID 21496693, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Twenty parts of a 3.13M methylmagnesium chloride solution in tetrahydrofuran was added dropwise to a solution of 20 parts of 2-(4-chloro-2-fluorophenyl)-4,5,6,7-tetrahydro-2 H-isoindole-1,3-dione in 200 parts of anhydrous tetrahydrofuran at 0° C over 1/2 hour. After stirring for 2 hours at 0° , 10 parts of a saturated aqueous ammonium chloride was added dropwise at 0°, resulting in a granular precipitate. After filtering the precipitate, the filtrate was evaporated at 300 mm. Hg and 50° to give 23.5 parts of 2-(4-chloro-2-fluorophenyl) -2,3,4,5,6,7-hexahydro-3-hydroxy-3methyl-1H-isoindol-1-one as indicated in particular by adsorption in the infrared spectrum of 1690 cm-1 (amide) and 3300 cm-1 (hydroxyl) and in the nuclear magnetic resonance spectrum of 4.6δ (1H, hydroxyl) and 1.1δ (3H, singlet methyl).

Workup

  1. customresulting in a granular precipitate
  2. filtrationAfter filtering the precipitate
  3. customthe filtrate was evaporated at 300 mm. Hg and 50°

Sources & evidence

ORD record
ord-0aee8768703c4f41bacb002c15ab6d19
Source dataset
uspto-grants-1976_11
Patent number
US03992189

Reaction notes

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