Hydrochloric Acid → Glycine, N-(3-nitrobenzoyl)-

HRID 378119Notes

Reaction equation

HRID 378119 reaction equation
[NH2:1][CH2:2][C:3]([OH:5])=[O:4].[OH-].[K+].[N+:8]([C:11]1[CH:12]=[C:13]([CH:17]=[CH:18][CH:19]=1)[C:14](Cl)=[O:15])([O-:10])=[O:9].Cl>O.C(#N)C>[N+:8]([C:11]1[CH:12]=[C:13]([CH:17]=[CH:18][CH:19]=1)[C:14](=[O:15])[NH:1][CH2:2][C:3]([OH:5])=[O:4])([O-:10])=[O:9]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 750GlycineHCID 8495Benzoyl chloride, 3-nitro-HCID 14797Potassium Hydroxide

Product 1

HCID 94858Glycine, N-(3-nitrobenzoyl)-Yield 82.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of glycine (200 g) and KOH (200 g) in water (1000 ml) at 0° C. was treated dropwise with a solution of m-nitrobenzoyl chloride (100 g) in acetonitrile (100 ml). The reaction was allowed to warm to room temperature and was stirred for 4 hours. 12N aqueous HCl was added until pH<2. The reaction was allowed to stand overnight at room temperature. The resulting solid was filtered and washed with water (2×250 ml) and dried in vacuo at 60° C. 100 g of m-nitrohippuric acid was isolated. MS, 1H-NMR and CHN analysis were consistent with the desired product.

Workup

  1. waitto stand overnight at room temperature
  2. filtrationThe resulting solid was filtered
  3. washwashed with water (2×250 ml)
  4. customdried in vacuo at 60° C

Sources & evidence

ORD record
ord-41d8df0f332f499b89e651a9a30af4f3
Source dataset
uspto-grants-2000_02
Patent number
US06028223

Reaction notes

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