Ammonia → 3-Amino-4-methoxycyclobut-3-ene-1,2-dione

HRID 1058860Notes

Reaction equation

HRID 1058860 reaction equation
[CH3:1][O:2][C:3]1[C:4](=[O:10])[C:5](=[O:9])[C:6]=1OC.[NH3:11]>CO>[NH2:11][C:6]1[C:5](=[O:9])[C:4](=[O:10])[C:3]=1[O:2][CH3:1]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 1232273-Cyclobutene-1,2-dione, 3,4-dimethoxy-

Product 1

HCID 134522053-Amino-4-methoxycyclobut-3-ene-1,2-dioneYield 75%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3,4-Dimethoxy-3-cyclobutene-1,2-dione (1.3 g, 9.2 mmol) in of MeOH (10.0 ml) was treated with aqueous ammonia (10.0 ml of a 2.0M solution) and stirred at ambient temperature for 2 h. The yellow precipitate thus formed was recovered by filtration, washed with MeOH and Et2O and dried in vacuo to afford the title compound (0.87 g, 75%) as an amorphous yellow powder δH (d6 DMSO) 8.32 (2H, br s), 4.28 (3H, s). m/z (ES+, 70V) 127 (MH+).

Workup

  1. customThe yellow precipitate thus formed
  2. filtrationwas recovered by filtration
  3. washwashed with MeOH and Et2O
  4. customdried in vacuo

Sources & evidence

ORD record
ord-48bcabd897a3402484b58f9590703c7a
Source dataset
uspto-grants-2003_02
Patent number
US06518283B1

Reaction notes

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