Methylamine → N-(3-Methylaminocarbonyl-5-nitrobenzoyl)-glycine methylammonium salt

HRID 1606662Notes

Reaction equation

HRID 1606662 reaction equation
[CH3:1][NH2:2].CO[C:5]([C:7]1[CH:8]=[C:9]([CH:17]=[C:18]([N+:20]([O-:22])=[O:21])[CH:19]=1)[C:10]([NH:12][CH2:13][C:14]([OH:16])=[O:15])=[O:11])=[O:6]>CO>[CH3:10][NH3+:12].[CH3:1][NH:2][C:5]([C:7]1[CH:8]=[C:9]([CH:17]=[C:18]([N+:20]([O-:22])=[O:21])[CH:19]=1)[C:10]([NH:12][CH2:13][C:14]([O-:16])=[O:15])=[O:11])=[O:6]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 21427264N-(3-Methoxycarbonyl-5-nitrobenzoyl)-glycine

Product 1

HCID 131710164N-(3-Methylaminocarbonyl-5-nitrobenzoyl)-glycine methylammonium salt

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

15 ml. of liquid methylamine is added at 0° C. to 42.3 g. (0.15 mole) of N-(3-methoxycarbonyl-5-nitrobenzoyl)-glycine (VIa) in 150 ml. of methanol; the reaction mixture is stored for 3 days at room temperature. Then, the mixture is concentrated to dryness under vacuum, and the residue is refluxed with absolute alcohol. After cooling, the reaction mixture is filtered, washed with alcohol and dried under vacuum. Yield: 43.2 g. M.P. 216°-217°C.

Workup

  1. concentrationThen, the mixture is concentrated to dryness under vacuum
  2. temperaturethe residue is refluxed with absolute alcohol
  3. temperatureAfter cooling
  4. filtrationthe reaction mixture is filtered
  5. washwashed with alcohol
  6. customdried under vacuum

Sources & evidence

ORD record
ord-5ec72ba4f3654dd887184b7116773530
Source dataset
uspto-grants-1976_04
Patent number
US03953501

Reaction notes

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