Oxalyl chloride → HCID 22046687, compound

HRID 1830984Notes

Reaction equation

HRID 1830984 reaction equation
[N+:1]([C:4]1[C:12]([O:13][CH3:14])=[C:11]([CH3:15])[C:10]([O:16][CH3:17])=[CH:9][C:5]=1[C:6]([OH:8])=O)([O-:3])=[O:2].C(Cl)(=O)C(Cl)=O.CC1[C:33](OC)=[CH:32][C:28](C(Cl)=O)=[C:27]([N+:36]([O-])=O)[C:26]=1[O:39]C.N1(CO)CCCC1>CN(C=O)C.C(Cl)Cl>[CH3:15][C:11]1[C:10]([O:16][CH3:17])=[CH:9][C:5]([C:6]([N:36]2[CH2:33][CH2:32][CH2:28][CH:27]2[CH2:26][OH:39])=[O:8])=[C:4]([N+:1]([O-:3])=[O:2])[C:12]=1[O:13][CH3:14]

Participants

7

Reactant 4

HCID 65578Oxalyl chlorideHCID 2331391PyrrolidinemethanolHCID 22046651HCID 22046651, compoundHCID 22046727HCID 22046727, compound

Product 1

HCID 22046687HCID 22046687, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent3×

Procedure

A catalytic amount of DMF (2 drops) was added to a stirred solution of 189 (3.96 g, 15.32 mmol) and oxalyl chloride (2.14 g, 16.85 mmol) in dry CH2Cl2 (50 mL) under a nitrogen atmosphere. The reaction mixture was allowed to stir overnight and the resulting acid chloride used directly in the next stage of the procedure. 4-methyl-3,5-dimethoxy-2-nitro-benzoyl chloride in anhydrous DCM (50 mL) was added dropwise over 0.5 hours to a stirring solution of pyrrolidine methanol (1.55 g, 15.32 mmol, 1.1 eq) and TEA (3.87 g, 38.3 mmol, 2.5 eq) in anhydrous DCM (50 mL) at 0° C. under a nitrogen atmosphere and the reaction mixture was allowed to stir overnight at room temperature. The reaction mixture was washed with 1 N HCl (2×100 mL), and the organic layer was washed with distilled H2O (2×100 mL), brine (2×100 mL) and dried over anhydrous MgSO4. Evaporation of excess solvent yielded a yellow glass (190) (2.13 g, 6.56 mmol, 43% -2 steps); 1H NMR (270 MHz, CDCl3) δ6.61 (s, 1H), 4.30-4.28 (m, 1H), 3.91 (s, 3H), 3.89 (s, 3H), 3.83-3.68 (m, 2H), 3.46-3.26 (m, 2H), 2.19 (s, 3H), 1.94-1.68 (m, 4H); 13C NMR (67.8 MHz, CDCl3) δ167.85, 161.15, 152.62, 135.70, 132.32, 123.17, 103.70, 65.87, 62.61, 61.37, 56.36, 50.20, 28.41, 24.50, 9.34.

Workup

  1. stirringto stir overnight at room temperature
  2. washThe reaction mixture was washed with 1 N HCl (2×100 mL)
  3. washthe organic layer was washed with distilled H2O (2×100 mL), brine (2×100 mL)
  4. dry with materialdried over anhydrous MgSO4
  5. customEvaporation of excess solvent

Sources & evidence

ORD record
ord-65169b7873a04f4aaa65050f371c6203
Source dataset
uspto-grants-2006_06
Patent number
US07067511B2

Reaction notes

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