Citric Acid → N-methoxy-N-methylbenzo[d][1,3]dioxole-5-carboxamide

HRID 486526Notes

Reaction equation

HRID 486526 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:13]1[O:24][C:23]2[CH:22]=[CH:21][C:17]([C:18]([OH:20])=O)=[CH:16][C:15]=2[O:14]1.Cl.[CH3:26][NH:27][O:28][CH3:29].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(Cl)Cl.C(N(CC)CC)C>[CH3:29][O:28][N:27]([CH3:26])[C:18]([C:17]1[CH:21]=[CH:22][C:23]2[O:24][CH2:13][O:14][C:15]=2[CH:16]=1)=[O:20]

Participants

7

Reactant 4

HCID 311Citric AcidHCID 71961,3-Benzodioxole-5-carboxylic acidHCID 682631,1'-CarbonyldiimidazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)

Product 1

HCID 10921728N-methoxy-N-methylbenzo[d][1,3]dioxole-5-carboxamideYield 97%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

1,1'-Carbonyl-diimidazole (48.8 g) was added portionwise within 30 minutes under argon and while stirring to a suspension of 50.0 g of 3,4-methylenedioxy-benzoic acid in 500 ml of methylene chloride. The resulting clear solution was stirred at room temperature for 2 hours and added dropwise within 30 minutes to 42 ml of triethylamine. Thereafter, 29.4 g of N,O-dimethylhydroxylamine hydrochloride were added and the mixture was stirred at room temperature overnight. After the addition of 800 ml of 30% citric acid solution the mixture was extracted twice with 300 ml of methylene chloride each time. The organic phases were washed in succession with 300 ml of 30% citric acid solution, 500 ml of saturated sodium hydrogen carbonate solution and 300 ml of saturated sodium hydrogen carbonate solution. The organic phases were combined, dried with MgSO4 and freed from solvent. 60.9 g (97%) of N-methoxy-N-methyl-1,3-benzodioxol-5-carboxamide were isolated as a pale yellow oil.

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. extractionwas extracted twice with 300 ml of methylene chloride each time
  3. washThe organic phases were washed in succession with 300 ml of 30% citric acid solution, 500 ml of saturated sodium hydrogen carbonate solution and 300 ml of saturated sodium hydrogen carbonate solution
  4. dry with materialdried with MgSO4

Sources & evidence

ORD record
ord-c21c184a22184952b57c019aff91c935
Source dataset
uspto-grants-1994_03
Patent number
US05292732

Reaction notes

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