Hydrochloric Acid → HCID 22001065, compound

HRID 747803Notes

Reaction equation

HRID 747803 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-0bc7d75fad2645578e24cdb34c1121af
Source dataset
uspto-grants-2008_07
Patent number
US07399460B2

Reaction notes

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