4-Hydroxy-3-nitrophenylacetic acid → (3-Amino-4-hydroxyphenyl)acetic acid
Reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][C:3]=1[N+:12]([O-])=O.C([O-])(O)=O.[Na+]>O>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][C:3]=1[NH2:12]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
92.4 g of 4-hydroxy-3-nitrophenylacetic acid are suspended in a solution constituted by 785 ml of H2O and 21.2 g of NaHCO3. 5 g of a catalyst constituted by 5% Pd-on-carbon are suspended in the solution, which is then hydrogenated at ambient temperature for 4 hours, to obtain 4-hydroxy-3-aminophenylacetic acid. The catalyst is separated by filtration in a nitrogen environment, and the aqueous solution is used for the reaction with 4-fluorobenzoyl chloride, which is carried out in the following manner: the aqueous solution is cooled to 5° C. in a nitrogen environment, 460 ml of t-butylmethylether are added, and then 74 ml of 4-fluorobenzoyl chloride dissolved in 170 ml of t-butylmethylether are fed slowly.
Sources & evidence
- ORD record
- ord-4acfd799b18b41d5862c1f4a7e0f1151
- Source dataset
- uspto-grants-1987_03
- Patent number
- US04652654
Reaction notes
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