Methylamine → HCID 67264031, compound

HRID 1041493Notes

Reaction equation

HRID 1041493 reaction equation
C[O:2][C:3]([C:5]1[CH:13]=[CH:12][C:8]2[O:9][CH2:10][O:11][C:7]=2[C:6]=1[NH2:14])=O.CN.[C:17]([Cu])#[N:18]>>[CH3:17][NH:18][C:3]([C:5]1[CH:13]=[CH:12][C:8]2[O:9][CH2:10][O:11][C:7]=2[C:6]=1[NH2:14])=[O:2]

Participants

4

Reactant 3

HCID 6329MethylamineHCID 596107HCID 596107, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 67264031HCID 67264031, compound

Procedure

4-Amino-benzo[1,3]dioxole-5-carboxylic acid methylamide was prepared by heating a mixture of 4-amino-benzo[1,3]dioxole-5-carboxylic acid methyl ester (198 mg, 1.01 mmol, Dallacker, Franz, et al. Justus Liebigs Ann Chem 1966, 694 117-22) with 2.0 M methanolic MeNH2 (7 mL, 14 mmol) and CuCN (1.42 g, 28.6 mmol) to 50° C. for 72 h. Excess catalyst was removed by filtration; filtrate was extracted into CH2Cl2, washed with water and dried by passing through a plug of Na2SO4. Evaporation of solvent afforded a white powder (187 mg, 95%) that was used in subsequent steps without further purification.

Workup

  1. temperatureby heating
  2. customExcess catalyst was removed by filtration
  3. extractionfiltrate was extracted into CH2Cl2
  4. washwashed with water
  5. customdried
  6. customEvaporation of solvent

Sources & evidence

ORD record
ord-ead4cabdd93c4760b807d6d96564f8ab
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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