Acetic Acid → ethyl N-[4-(hydroxymethyl)-2-nitrophenyl]glycine

HRID 1723097Notes

Reaction equation

HRID 1723097 reaction equation
[CH2:1]([N:3]([C:8]1[CH:13]=[CH:12][C:11]([CH:14]=[O:15])=[CH:10][C:9]=1[N+:16]([O-:18])=[O:17])[CH2:4][C:5]([OH:7])=[O:6])[CH3:2].C(O)C.[BH4-].[Na+].C(O)(=O)C>O>[CH2:1]([N:3]([C:8]1[CH:13]=[CH:12][C:11]([CH2:14][OH:15])=[CH:10][C:9]=1[N+:16]([O-:18])=[O:17])[CH2:4][C:5]([OH:7])=[O:6])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 702EthanolHCID 4311764Sodium borohydrideHCID 86743322ethyl N-(4-formyl-2-nitrophenyl)glycine

Product 1

HCID 70396304ethyl N-[4-(hydroxymethyl)-2-nitrophenyl]glycineYield 70.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(a-2) To a stirred solution of 47.8 parts of ethyl N-(4-formyl-2-nitrophenyl)glycine in 280 parts of ethanol were added in small portions 3.8 parts of sodium tetrahydroborate. The whole was stirred for 30 minutes at room temperature. The reaction mixture was decomposed by a solution of 12 parts of acetic acid in 50 parts of water. The mixture was concentrated. The product was extracted with dichloromethane. The extract was dried, filtered and evaporated. The residue was crystallized from 2-propanol. The product was filtered off and dried, yielding 34.1 parts (70.6%) of ethyl N-[4-(hydroxymethyl)-2-nitrophenyl]glycine (int. 30).

Workup

  1. concentrationThe mixture was concentrated
  2. extractionThe product was extracted with dichloromethane
  3. customThe extract was dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was crystallized from 2-propanol
  7. filtrationThe product was filtered off
  8. customdried

Sources & evidence

ORD record
ord-395036b3f628442ea1aaf8df603af093
Source dataset
uspto-grants-1989_08
Patent number
US04859684

Reaction notes

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