HCID 131722394, compound → HCID 15338726, compound

HRID 635908Notes

Reaction equation

HRID 635908 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[O:10][C:9]([CH3:15])([CH3:14])[CH2:8][C:7]2=[N:16]O)([OH:3])=[O:2].[H][H]>CO.N.[Ni]>[NH2:16][CH:7]1[C:6]2[C:11](=[CH:12][CH:13]=[C:4]([C:1]([OH:3])=[O:2])[CH:5]=2)[O:10][C:9]([CH3:15])([CH3:14])[CH2:8]1

Participants

6

Reactant 2

HCID 131722394HCID 131722394, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 15338726HCID 15338726, compound

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 222AmmoniaSolventHCID 887MethanolSolvent

Procedure

35.2 g (0.15 mol) of 6-carboxy-2,2-dimethyl-4-chromanone oxime are dissolved in 300 ml of methanol by addition of 600 ml of concentrated aqueous ammonia and, after addition of a few grams of Raney nickel catalyst, hydrogenated at 80° C. for 10 hours under 100 atm hydrogen pressure. After filtering off the catalyst, approximately ¾ of the solvent is distilled off in a rotary evaporator. The crystalline precipitate of 4-amino-6-carboxy-2,2-dimethylchroman is filtered off.

Workup

  1. filtrationAfter filtering off the catalyst, approximately ¾ of the solvent
  2. distillationis distilled off in a rotary evaporator
  3. filtrationThe crystalline precipitate of 4-amino-6-carboxy-2,2-dimethylchroman is filtered off

Sources & evidence

ORD record
ord-067e89bf47c44bb6aab788bc398efa49
Source dataset
uspto-grants-2001_02
Patent number
US06191164B1

Reaction notes

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