p-Toluenesulfonic acid → 2-(6-methylquinolin-2-yl)benzoic Acid

HRID 1956768Notes

Reaction equation

C1(OC2C=CC=CC=2)C=CC=CC=1.[C:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:23]1[CH:32]=[C:31](C(O)=O)[C:30]2[C:25](=[CH:26][CH:27]=[C:28]([CH3:36])[CH:29]=2)[N:24]=1)([OH:16])=[O:15].C1(C)C=CC(S(O)(=O)=O)=CC=1.[OH-].[Na+]>O>[CH3:36][C:28]1[CH:29]=[C:30]2[C:25](=[CH:26][CH:27]=1)[N:24]=[C:23]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[C:14]([OH:16])=[O:15])[CH:32]=[CH:31]2

Participants

Conditions

Temperature: 160 °C

Procedure

To 1 ml of diphenyl ether were added 0.2 g of the 2-(2-carboxyphenyl)-6-methyl-4-quinolinecarboxylic acid obtained in Example 2. After adding 123 mg of p-toluenesulfonic acid, the mixture was heated at 160° C. for 1 hour. Then the reaction mixture was poured into water, made alkaline by adding sodium hydroxide and washed with ethyl acetate. The aqueous layer was neutralized with 3M hydrochloric acid until a precipitate was formed. After extracting with ethyl acetate, 80 mg of 2-(6-methylquinolin-2-yl)benzoic acid were obtained. NMR (270 MHz, CD3OD): δ 7.58-8.32 (m,9H); 2.58 (s,3H).

Workup

washwashed with ethyl acetate
customwas formed
extractionAfter extracting with ethyl acetate

Sources & evidence

ORD record: ord-ef4c377989814ab4bab181f5c2f0cee3
Source dataset: uspto-grants-1998_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05780634

Reaction notes

Loading…