Methylamine → HCID 66752016, compound
Reaction equation
[CH3:1][N:2]([CH:4]=[C:5]1[C:18]2[C:9](=[N:10][C:11]3[C:16]([N:17]=2)=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:8](=[O:19])[O:7][C:6]1=[O:20])C.CN>>[CH3:1][N:2]1[CH:4]=[C:5]([C:6]([OH:7])=[O:20])[C:18]2[C:9](=[N:10][C:11]3[C:16]([N:17]=2)=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:8]1=[O:19]Participants
3
Procedure
From 17d and methylamine, as for 18d except that, after reaction, the volatiles were removed at reduced pressure to leave the methylamine salt of 18z as a yellow-brown solid. This was suspended in a small amount of water and 10% sodium hydroxide was added dropwise, with stirring, until a solution was obtained. This was acidified with a minimum amount of concentrated hydrochloric acid and the solid which separated was filtered and washed with water to give the free acid as a yellow solid (52%), mp >300° C. (from dimethyl sulfoxide/1,4-dioxane). 1H NMR (d6-DMSO): δ 3.66 (s, 3H, NCH3), 7.97 (t, J=7.5 Hz, 1H), 8.08 (t, J=7.6 Hz, 1H), 8.25-8.32 (m, 2H), 8.79 (s, 1H), 14.03 (br s, 1H, COOH).
Workup
- customthe volatiles were removed at reduced pressure