Glycine → 4-carboxy-N-(carboxymethyl)phthalimide

HRID 858339Notes

Reaction equation

HRID 858339 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[O:12])[O:10][C:8](=O)[C:7]2=[CH:13][CH:14]=1)([OH:3])=[O:2].[NH2:15][CH2:16][C:17]([OH:19])=[O:18]>C(O)(=O)C>[C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[O:12])[N:15]([CH2:16][C:17]([OH:19])=[O:18])[C:8](=[O:10])[C:7]2=[CH:13][CH:14]=1)([OH:3])=[O:2]

Participants

4

Reactant 2

HCID 750GlycineHCID 11089Trimellitic anhydride

Product 1

HCID 6768334-carboxy-N-(carboxymethyl)phthalimide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4-carboxyphthalic anhydride (benzene tricarboxylic acid anhydride) (1.0 g, 0.0052 mol), glycine (0.3907 g, 0.0052 mol) and 50–60 mls of glacial acetic acid were added to a 100 ml round-bottom flask equipped with a reflux condenser, heating mantle and stir plate. The system was placed under a N2 atmosphere and heated to a gentle reflux. The progress of the reaction was monitored by TLC. After 7 hours the clear colourless solution was cooled to room temperature. The resulting white precipitate was filtered through a Buchner funnel and washed three times with 10 mls of distilled water. This crude material was recrystallized in EtOH/H2O to afford the desired product as a powdery white solid. The filtrate was evaporated under vacuum using a rotary evaporator. The crude material was recrystallized from EtOH/H2O to yield a second batch of white powdery product. Individual batches were dried in air for 24 hours and then in vacuo for 48–72 hours to afford 100 in a combined yield of 1.02 g (78%): mp=262–265° C.; Rf 0.70 (A): Rf 0.47 (B): Rf 0.20 (D): 1H NMR (DMSO-d6) δ 4.33 (s, 2H), 8.02 (d, J=7.8 Hz, 1H), 8.24 (bs, 1H), 8.36 (d, J=7.8 Hz, 1H); MS m/z (rel intensity) 249 (13), 248 (100), 204 (36); IR (cm−1): 2750–3300 (OH), 3052 (C═CH), 2671 (C—H), 1776 (C═O), 1731 (C═O), 1705 (C═O), 1620 (C═C), 1420 (C═C), 1300 (C—O), 1122 (C—O), 746 (C═CH).

Workup

  1. customequipped with a reflux condenser
  2. temperatureheating mantle
  3. temperatureheated to a gentle reflux
  4. filtrationThe resulting white precipitate was filtered through a Buchner funnel
  5. washwashed three times with 10 mls of distilled water
  6. customThis crude material was recrystallized in EtOH/H2O

Sources & evidence

ORD record
ord-48a27ebdbf6b4cd395da80ccb2d182c5
Source dataset
uspto-grants-2006_12
Patent number
US07148352B2

Reaction notes

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