HCID 18429161, compound → HCID 15040326, compound

HRID 383027Notes

Reaction equation

HRID 383027 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH2:13][OH:14])[CH:7]=[C:8]([CH:12]=1)[C:9]([OH:11])=[O:10])([O-])=O.[H][H]>O1CCOCC1.O.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([CH2:13][OH:14])[CH:7]=[C:8]([CH:12]=1)[C:9]([OH:11])=[O:10]

Participants

6

Reactant 2

HCID 18429161HCID 18429161, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 15040326HCID 15040326, compoundYield 121.4%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

5-Nitro-3-hydroxymethyl benzoic acid (39.6 g, 0.20 mol) was suspended in a mixture of dioxane (25 ml) and water (50 ml). Palladium on carbon (5%) was added and the mixture was hydrogenated in a Parr apparatus until the stoichiometric amount of hydrogen had been consumed. The catalyst was filtered off and the filtrate passed into concentrated hydrochloric acid (12M, 17 ml). The filtrate was evaporated to dryness to give 40.6 g of a crystalline product. Yield is almost quantitative. The product was used without further purification.

Workup

  1. customhad been consumed
  2. filtrationThe catalyst was filtered off
  3. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-6a0c8f9d767643c7b5a6f921550c316b
Source dataset
uspto-grants-2001_10
Patent number
US06310243B1

Reaction notes

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