Sodium Carbonate → 2H-Isoindole-2-acetamide, 1,3-dihydro-1,3-dioxo- (9CI)

HRID 1451835Notes

Reaction equation

HRID 1451835 reaction equation
Cl.[NH2:2][CH2:3][C:4]([NH2:6])=[O:5].C(=O)([O-])[O-].[Na+].[Na+].C(N1[C:22](=[O:23])[C:21]2=[CH:24][CH:25]=[CH:26][CH:27]=[C:20]2[C:19]1=[O:28])(OCC)=O>O.C(O)C>[CH:25]1[CH:24]=[C:21]2[C:22]([N:2]([CH2:3][C:4]([NH2:6])=[O:5])[C:19](=[O:28])[C:20]2=[CH:27][CH:26]=1)=[O:23]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 31187N-CarbethoxyphthalimideHCID 2723639Glycinamide hydrochloride

Product 1

HCID 210532H-Isoindole-2-acetamide, 1,3-dihydro-1,3-dioxo- (9CI)Yield 65.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of glycinamide hydrochloride (2.20 g, 20.0 mmoL) and sodium carbonate (2.54 g, 24 mmoL) in 25 mL of water is added N-carbethoxyphthalimide (4.38 g, 20.0 mmoL). The resulting suspension is stirred for 1.5 hour and then filtered to afford 3.22 g (79%) of the crude product as a white powder. The crude product is slurried in 200 mL of refluxing ethanol. The resulting suspension after cooling to room temperature is filtered and the solid dried in vacuo (60° C., <1 mm) to afford 2.65 g (65%) of N-phthaloylglycinamide as a white powder: mp 199°-201° C.; 1H NMR (DMSO-d6) δ 8.00-7.8 (m, 4 H, Ar), 7.70 (br s, 1 H, CONH2), 7.26 (br s, 1 H, CONH2), 4.16 (s, 2 H, CH2); 13C NMR (DMSO-d6) δ 167.8, 167.5, 134.4, 131.7, 123.1, 39.9. Anal. Calcd for C11H10N2O3. Theoretical: C, 60.55; H, 4.62; N, 12.84. Found: C, 60.49; H, 4.59; N, 12.82.

Workup

  1. filtrationfiltered
  2. customto afford 3.22 g (79%) of the crude product as a white powder
  3. filtrationis filtered
  4. customthe solid dried in vacuo (60° C., <1 mm)

Sources & evidence

ORD record
ord-48878a68fa96451a941278d4aa1811b6
Source dataset
uspto-grants-1997_02
Patent number
US05605914

Reaction notes

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