6-Aminohexanoic Acid → 1,3-Dihydro-1,3-dioxo-2H-isoindole-2-hexanoic acid

HRID 20904

Reaction equation

HRID 20904 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8].[C:10]1(=O)[O:15][C:13](=[O:14])[C:12]2=[CH:16][CH:17]=[CH:18][CH:19]=[C:11]12.C(N(CC)CC)C>C1(C)C=CC=CC=1>[O:14]=[C:13]1[C:12]2[C:11](=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:10](=[O:15])[N:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([OH:9])=[O:8]

Participants

5

Reactant 3

HCID 5646-Aminohexanoic AcidHCID 6811Phthalic AnhydrideHCID 8471Triethylamine

Product 1

HCID 781851,3-Dihydro-1,3-dioxo-2H-isoindole-2-hexanoic acidYield 93.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

6-amino hexanoic acid (39a) (13.1 g, 100 mmol) and phthalic anhydride (40) (14.8 g, 100 mmol) were mixed in toluene (150 mL). To the suspension was added triethyl amine (13 mL). The suspension was refluxed using Dean-stark for 16 h. When collection of water ceased, the reaction was cooled and evaporated to dryness. The residue was suspended in water and conc. hydrochloric acid (1.5 mL) was added. The suspension was stirred for 30 mins and filtered. The precipitate was washed with water and dried over sodium sulfate to afford compound 41a (24.5 g, 93%) which was used as such for the next step.

Workup

  1. temperatureThe suspension was refluxed
  2. customWhen collection of water
  3. temperaturethe reaction was cooled
  4. customevaporated to dryness
  5. additionconc. hydrochloric acid (1.5 mL) was added
  6. filtrationfiltered
  7. washThe precipitate was washed with water
  8. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-4706a98e50fd4e15a3f76d02470aa718
Source dataset
uspto-grants-2010_06
Patent number
US07745608B2

Linked notes

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