Hydrochloric Acid → HCID 22001065, compound

HRID 324921Notes

Reaction equation

HRID 324921 reaction equation
[CH3:1][C:2]([CH3:17])=[CH:3][CH2:4][CH2:5][N:6]1[C:10](=[O:11])[C:9]2=[CH:12][CH:13]=[CH:14][CH:15]=[C:8]2[C:7]1=[O:16].[N:18]([O:20]CCC(C)C)=O.[ClH:26]>>[Cl:26][C:2]([CH3:17])([CH3:1])[CH:3]([N:18]=[O:20])[CH2:4][CH2:5][N:6]1[C:7](=[O:16])[C:8]2=[CH:15][CH:14]=[CH:13][CH:12]=[C:9]2[C:10]1=[O:11]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 8053Isoamyl NitriteHCID 132638822-(4-Methylpent-3-en-1-yl)-1H-isoindole-1,3(2H)-dione

Product 1

HCID 22001065HCID 22001065, compound

Procedure

To a cooled (0-5° C.) solution of 4-methyl-1-(phthalimido)-3-pentene (5.0 g, 0.022 mol) and isoamyl nitrite (13.0 g, 15 mL, 0.11 mol) was added concentrated hydrochloric acid (4.0 mL, 0.04 mol) with stirring. The reaction mixture was maintained below 5° C. during the addition and stirred at 5° C. for an additional 2 h. The solid formed was filtered and washed with cold ether:ethanol (3:1, 150 mL) and dried. Yield: 4.72 g (72.8%). It was crystallized from acetonitrile. mp 140-141° C. MS: (M+H)+=296.0.

Workup

  1. temperatureThe reaction mixture was maintained below 5° C. during the addition
  2. stirringstirred at 5° C. for an additional 2 h
  3. customThe solid formed
  4. filtrationwas filtered
  5. washwashed with cold ether:ethanol (3:1, 150 mL)
  6. customdried
  7. customIt was crystallized from acetonitrile

Sources & evidence

ORD record
ord-5f59cf6d16e9494fbaaff1ab7ce6954b
Source dataset
uspto-grants-2001_04
Patent number
US06221334B1

Reaction notes

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