Methylamine → HCID 67264031, compound

HRID 1687833Notes

Reaction equation

HRID 1687833 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-6e7b826f10b94b0799892a5f680ecd1a
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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