Oxalic Acid → HCID 9837977, compound

HRID 1655102Notes

Reaction equation

HRID 1655102 reaction equation
[C:1]([OH:6])(=[O:5])[C:2]([OH:4])=[O:3].[CH3:7][C:8]1[CH:12]=[C:11]([CH:13]2[CH2:17][CH2:16][CH2:15][N:14]2[CH3:18])[O:10][N:9]=1>C(OCC)C>[C:1]([OH:6])(=[O:5])[C:2]([OH:4])=[O:3].[CH3:7][C:8]1[CH:12]=[C:11]([C@@H:13]2[CH2:17][CH2:16][CH2:15][N:14]2[CH3:18])[O:10][N:9]=1

Participants

4

Reactant 2

HCID 971Oxalic AcidHCID 15186066HCID 15186066, compound

Product 1

HCID 9837977HCID 9837977, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of oxalic acid (51 mg, 0.57 mmol) in diethyl ether was added dropwise to a stirring solution of 3-methyl-5-(1-methyl-2-pyrrolidinyl)-isoxazole (62.8 mg, 0.38 mmol), from Example 2a, in diethyl ether. After 0.5 hour of stirring at ambient temperature, the reaction flask became coated with a glass-like clear colorless solid. The diethyl ether was evaporated and the solid was triturated several times with diethyl ether to give, after evaporation of the solvent in vacuo, 102 mg of the title compound (2b). MS (DCl/NH3) m/e 167 (M+H)+, 184 (M+NH4)+. 1H NMR (D2O) δ: 2.11-2.33 (m, 3H), 2.31 (s, 3H), 2.49-2.60 (m, 1H), 2.48 (dd, 2H), 4.92 (t, 1H), 6.52 (s, 1H). Anal. calcd. for C10H13NO5.0.2H2O.0.2C2H2O 2 : C, 48.65; H, 6.16; N, 9.95. Found: C, 48.80; H, 5.90; N, 9.77.

Workup

  1. customThe diethyl ether was evaporated
  2. customthe solid was triturated several times with diethyl ether
  3. customto give
  4. customafter evaporation of the solvent in vacuo, 102 mg of the title compound (2b)

Sources & evidence

ORD record
ord-31aa152bd6c544f7a48204873742d315
Source dataset
uspto-grants-1995_04
Patent number
US05409946

Reaction notes

Loading…