Triethylamine → 4-[(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)methyl]benzoic acid

HRID 2305326Notes

Reaction equation

HRID 2305326 reaction equation
[NH2:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1.[C:12]([C:17]1[CH:27]=[CH:26][CH:25]=[C:19]2C(N[C:23](=[O:24])[C:18]=12)=O)(OCC)=[O:13].C(N(CC)CC)C>O1CCCC1>[C:23]1(=[O:24])[N:1]([CH2:2][C:3]2[CH:4]=[CH:5][C:6]([C:7]([OH:9])=[O:8])=[CH:10][CH:11]=2)[C:12](=[O:13])[C:17]2=[CH:27][CH:26]=[CH:25][CH:19]=[C:18]12

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 655264-(Aminomethyl)Benzoic AcidHCID 22254400Ethoxycarbonylphthalimide

Product 1

HCID 7475534-[(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)methyl]benzoic acidYield 77.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 10 g of 4-aminomethylbenzoic acid, 14.5 g of carbethoxyphthalimide, 9.2 ml of triethylamine and 140 ml of tetrahydrofuran is maintained for 72 hours at reflux temperature. The precipitate formed is isolated at room temperature; after washing with an aqueous acidic solution and drying, 14.5 g of product are obtained. M.p.=264° C.

Workup

  1. temperatureis maintained for 72 hours
  2. temperatureat reflux temperature
  3. customThe precipitate formed
  4. customis isolated at room temperature
  5. washafter washing with an aqueous acidic solution
  6. customdrying

Sources & evidence

ORD record
ord-e8d0dd511fcf4d2f8051009d86cb5b85
Source dataset
uspto-grants-2002_08
Patent number
US06440956B1

Reaction notes

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