Methanol → HCID 21492496, compound

HRID 1973049Notes

Reaction equation

HRID 1973049 reaction equation
[N+:1]([C:4]1[CH:20]=[CH:19][C:7]([O:8][C:9]2[CH:17]=[C:13]([C:14]([OH:16])=[O:15])[C:12]([OH:18])=[CH:11][CH:10]=2)=[CH:6][CH:5]=1)([O-])=O.CO.[H][H].NC1C=CC=C(C(O)=O)C=1OOC1C=CC=CC=1>C(O)C.[Ni].CC(N(C)C)=O>[NH2:1][C:4]1[CH:20]=[CH:19][C:7]([O:8][C:9]2[CH:17]=[C:13]([C:14]([OH:16])=[O:15])[C:12]([OH:18])=[CH:11][CH:10]=2)=[CH:6][CH:5]=1

Participants

8

Reactant 4

HCID 887MethanolHCID 214925045-(4-Nitrophenoxy)-salicylic acidHCID 54317397HCID 54317397, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21492496HCID 21492496, compound

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolventHCID 31374DimethylacetamideSolvent

Procedure

71 g of 5-(4-nitrophenoxy)-salicylic acid prepared in accordance with Example 1a were hydrogenated at 90° C/100 atms. in 400 ml of ethanol or methanol in the presence of 2.8 g of Raney nickel. The adsorption of hydrogen ceased after 3 hours at the longest. Following the addition of 100 ml of dimethyl acetamide, the catalyst was separated off under heat, water was added at 100° C until a haze began to form, after which the solution was heated for 20 minutes in the presence of 20 g of active carbon and the free aminophenoxy salicylic acid allowed to crystallise out after filtration, being obtained in a yield of 50 g (79% of the theoretical yield), m.p. 223° - 224° C.

Workup

  1. customwere hydrogenated at 90° C
  2. customthe catalyst was separated off
  3. temperatureunder heat
  4. additionwater was added at 100° C until a haze
  5. customto form
  6. temperatureafter which the solution was heated for 20 minutes in the presence of 20 g of active carbon
  7. customto crystallise out
  8. filtrationafter filtration
  9. custombeing obtained in a yield of 50 g (79% of the
  10. customtheoretical yield), m.p. 223° - 224° C.

Sources & evidence

ORD record
ord-3e8d812898c54659b1c2a3843b2d1a2d
Source dataset
uspto-grants-1976_12
Patent number
US03996197

Reaction notes

Loading…