Methylamine → HCID 66752016, compound

HRID 1785407Notes

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

Reactant 2

HCID 6329Methylamine

HCID 86601402HCID 86601402, compound

Product 1

HCID 66752016HCID 66752016, compound

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

Sources & evidence

ORD record: ord-be1f33b239d846cb9ce9363f7b3b5692
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07504507B2

Reaction notes

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