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

HRID 2403004Notes

Reaction equation

HRID 2403004 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-d31c937b6b8241d0b034b2c47f2f2f81
Source dataset
uspto-grants-2014_08
Patent number
US08796436B2

Reaction notes

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