Ammonium Hydroxide → (1-Carbamoylmethyl)acrylic acid

HRID 1586023Notes

Reaction equation

HRID 1586023 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 3 g (0.027 mol) 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 40. 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, 1H, 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 40
  5. customThe precipitate formed
  6. filtrationwas filtered off
  7. washwashed with a small portion of cold water
  8. customdried

Sources & evidence

ORD record
ord-a09d409e1e5d4b748d51b7d646bf9692
Source dataset
uspto-grants-1999_08
Patent number
US05942504

Reaction notes

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