Ammonium Hydroxide → (1-Carbamoylmethyl)acrylic acid

HRID 1489771

Reaction equation

HRID 1489771 reaction equation
[C:1]1(=[O:8])[O:7][C:5](=[O:6])[CH2:4][C:2]1=[CH2:3].[OH-].[NH4+:10]>O1CCCC1>[C:5]([CH2:4][C:2](=[CH2:3])[C:1]([OH:7])=[O:8])(=[O:6])[NH2:10]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 75110Itaconic Anhydride

Product 1

HCID 418291(1-Carbamoylmethyl)acrylic acidYield 40%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 3g (0.027mol) of itaconic anhydride in 30 ml of tetrahydrofuran, 3 ml of 28% ammonium hydroxide was added. After 1 hr. the reaction mixture was evaporated to dryness under reduced pressure. The residue was dissolved in 15 ml of water, then acidified to pH 2 with concentrated hydrochloric acid and allowed to stay overnight at 4°. The precipitate formed was filtered off, washed with a small portion of cold water and dried to give 1.4 g (40% yield) of the title compound melting at 153°-154° C.; NMR (DMSO-d6): 3.11 (s, 2H, CH2); 5.67,6.13 (s, s, 1H, 1H, CH); 6.7, 7.9 (broad s, s 1H, 1H, NH); 12.15 (broad s, 1 H, OH).

Workup

  1. additionwas added
  2. customthe reaction mixture was evaporated to dryness under reduced pressure
  3. dissolutionThe residue was dissolved in 15 ml of water
  4. waitto stay overnight at 4°
  5. customThe precipitate formed
  6. filtrationwas filtered off
  7. washwashed with a small portion of cold water
  8. customdried

Sources & evidence

ORD record
ord-d6aac4ff006f42e09e348650f1294a80
Source dataset
uspto-grants-1997_10
Patent number
US05679688

Linked notes

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