Sodium Hydroxide → 3-[[[2-(Methylamino)-2-oxoethyl]amino]carbonyl]-5-nitrobenzoic acid

HRID 1606660Notes

Reaction equation

HRID 1606660 reaction equation
[CH3:1][NH:2][C:3](=[O:21])[CH2:4][NH:5][C:6](=[O:20])[C:7]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[C:9]([C:16]([O:18]C)=[O:17])[CH:8]=1.O1CCOCC1.[OH-].[Na+]>O>[CH3:1][NH:2][C:3](=[O:21])[CH2:4][NH:5][C:6](=[O:20])[C:7]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[C:9]([C:16]([OH:18])=[O:17])[CH:8]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 214272733-Metoxycarbonyl-5-nitrobenzoyl-glycine methylamide

Product 1

HCID 30164953-[[[2-(Methylamino)-2-oxoethyl]amino]carbonyl]-5-nitrobenzoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

443.0 g. (1.5 moles) of N-(3-metoxycarbonyl-5-nitrobenzoyl-glycine methylamide in 5.5 l. of dioxane is agitated for 2 hours at room temperature with the addition of 3.3 l. of 0.5N sodium hydroxide solution. Thereafter, 400 ml. of water is added to the reaction mixture, the dioxane is distilled off under vacuum, and the acid is precipitated with concentrated hydrochloric acid, vacuum-filtered, washed free of salt with water, and dried under vacuum at 70° C. Yield: 408 g. M.P. 256- 257°C.

Workup

  1. distillationthe dioxane is distilled off under vacuum
  2. customthe acid is precipitated with concentrated hydrochloric acid
  3. filtrationvacuum-filtered
  4. washwashed free of salt with water
  5. customdried under vacuum at 70° C

Sources & evidence

ORD record
ord-cb64c463bc614f119a91f08de97a248f
Source dataset
uspto-grants-1976_04
Patent number
US03953501

Reaction notes

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