4-((Tetrahydropyran-4-yl)amino)-3-nitrobenzoic acid → 3-Amino-4-((tetrahydropyran-4-yl)amino)benzoic acid

反応式

[O:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8]2[CH:16]=[CH:15][C:11]([C:12]([OH:14])=[O:13])=[CH:10][C:9]=2[N+:17]([O-])=O)[CH2:3][CH2:2]1>C1COCC1.CO.[Pd]>[NH2:17][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][C:8]=1[NH:7][CH:4]1[CH2:5][CH2:6][O:1][CH2:2][CH2:3]1)[C:12]([OH:14])=[O:13]

参加物

実験手順

4-((Tetrahydropyran-4-yl)amino)-3-nitrobenzoic acid (see Working Example 4-1) (202 g, 0.76 mol) was dissolved in a solvent mixture of THF (2.2 L) and methanol (1.5 L), Pd/C (5%, wet, 20 g) was added, and hydrogenation was carried out under 5 atm. Hydrogen absorption stopped at 3 h, and after the system was purged with argon the catalyst was removed by filtration, and the filtrate was concentrated at reduced pressure to yield the title compound (180 g, quant.) as a dark gray solid.