Veratric Acid → HCID 20038699, compound

HRID 1904227Notes

Reaction equation

HRID 1904227 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[C:6]([OH:8])=O.C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:26][CH2:27][CH2:28][N:29]1[C:33]([CH3:34])=[CH:32][CH:31]=[C:30]1[CH3:35]>O1CCOCC1>[CH3:35][C:30]1[N:29]([CH2:28][CH2:27][NH:26][C:6](=[O:8])[C:5]2[CH:9]=[CH:10][C:11]([O:12][CH3:13])=[C:3]([O:2][CH3:1])[CH:4]=2)[C:33]([CH3:34])=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 7121Veratric AcidHCID 682631,1'-CarbonyldiimidazoleHCID 137700502-(2,5-Dimethyl-1H-pyrrol-1-yl)ethan-1-amine

Product 1

HCID 20038699HCID 20038699, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

9.1 g (0.05 mol) of 3,4-dimethoxybenzoic acid and 8.2 g (0.05 mol) of carbonyldiimidazole in 50 ml of dioxane are stirred at 60° C. for 15 min. After addition of 6.2 g (0.045 mol) of 1-(2-aminoethyl)2,5-dimethylpyrrole in 20 ml of dioxane to the mixture it is stirred at room temperature for 20 h, concentrated, and aqueous sodium bicarbonate solution is added and the mixture is extracted with methylene chloride. The extract is chromatographed over an alumina column, and the product is crystallized using ethyl acetate/ether/ligroin. Yield: 6.9 g (46% of theory), Melting point: 82°-84° C. Elemental analysis: C17H22N2O3 (302.37) calculated: C 67.5 H 7.3 N 9.3 O 15.9 found: C 67.3 H 7.2 N 8.8 O 16.6

Workup

  1. concentrationconcentrated
  2. additionaqueous sodium bicarbonate solution is added
  3. extractionthe mixture is extracted with methylene chloride
  4. customThe extract is chromatographed over an alumina column
  5. customthe product is crystallized

Sources & evidence

ORD record
ord-27e31a530e85439d80fcf8c94242876b
Source dataset
uspto-grants-1989_06
Patent number
US04837225

Reaction notes

Loading…