Triethylamine → HCID 53685514, compound

HRID 1589823Notes

Reaction equation

HRID 1589823 reaction equation
[Cl:1][C:2]1[C:7]([OH:8])=[C:6]([O:9][CH3:10])[CH:5]=[C:4]([N+:11]([O-])=O)[C:3]=1[CH2:14][C:15]([OH:17])=[O:16].C(N(CC)CC)C>CO.[Pd]>[Cl:1][C:2]1[C:7]([OH:8])=[C:6]([O:9][CH3:10])[CH:5]=[C:4]([NH2:11])[C:3]=1[CH2:14][C:15]([OH:17])=[O:16]

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 53755540HCID 53755540, compound

Product 1

HCID 53685514HCID 53685514, compoundYield 139%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To 2-chloro-3-hydroxy-4-methoxy-6-nitrophenylacetic acid (52 g) in methanol (600 ml) was added triethylamine (56 ml) and 10% palladium on carbon (4 g). The mixture was hydrogenated for 3 hours at 1.4 bar, filtered, evaporated and the residue crystallised to give the triethylamine salt of 2-chloro-3-hydroxy-4-methoxy-6-aminophenylacetic acid (64 g); NMR (DMSO-d6 /CD3COD/CF3COOD) 1.17(t,9H); 3.05(s,6H); 3.54(s,2H); 3.73(s,3H); 6.4(s,1H).

Workup

  1. filtrationfiltered
  2. customevaporated
  3. customthe residue crystallised

Sources & evidence

ORD record
ord-61239ed9daae48ec839f2c2df93e46e2
Source dataset
uspto-grants-1993_04
Patent number
US05200404

Reaction notes

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