Hydrochloric Acid → HCID 22001065, compound

HRID 456359Notes

Reaction equation

HRID 456359 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-db9272fcc54841b88676ea04e0f46721
Source dataset
uspto-grants-2007_03
Patent number
US07186397B2

Reaction notes

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