Thioanisole → 4-(4-(2-Methoxyphenoxy)-anilino)-3-cyano-6-methoxy-7-hydroxyquinoline

HRID 749059Notes

Reaction equation

HRID 749059 reaction equation
[CH3:1][O:2][C:3]1[CH:38]=[CH:37][CH:36]=[CH:35][C:4]=1[O:5][C:6]1[CH:34]=[CH:33][C:9]([NH:10][C:11]2[C:20]3[C:15](=[CH:16][C:17]([O:23]CC4C=CC=CC=4)=[C:18]([O:21][CH3:22])[CH:19]=3)[N:14]=[CH:13][C:12]=2[C:31]#[N:32])=[CH:8][CH:7]=1.C1(SC)C=CC=CC=1>FC(F)(F)C(O)=O>[CH3:1][O:2][C:3]1[CH:38]=[CH:37][CH:36]=[CH:35][C:4]=1[O:5][C:6]1[CH:34]=[CH:33][C:9]([NH:10][C:11]2[C:20]3[C:15](=[CH:16][C:17]([OH:23])=[C:18]([O:21][CH3:22])[CH:19]=3)[N:14]=[CH:13][C:12]=2[C:31]#[N:32])=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 7520ThioanisoleHCID 98274294-(4-(2-Methoxyphenoxy)-anilino)-3-cyano-6-methoxy-7-(benzyloxy)quinoline

Product 1

HCID 1358198314-(4-(2-Methoxyphenoxy)-anilino)-3-cyano-6-methoxy-7-hydroxyquinoline

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent2×

Procedure

The product from step (1) (7.2 g, 14.3 mmole) trifluoroacetic acid (40 ml) and thioanisole (8.38 ml, 71.5 mmole) was refluxed in a nitrogen atmosphere for 3 hours. After cooling the trifluoroacetic acid was removed by rotary evaporation and the oily residue was stirred with ice and water and basified with aqueous ammonia (S.G. 0.880). The resulting suspension was filtered and the solid was washed successively with water, ethyl acetate and diethyl ether and then dried to give 4-(4-(2-methoxyphenoxy)-anilino)-3-cyano-6-methoxy-7-hydroxyquinoline.

Workup

  1. customwas removed by rotary evaporation
  2. filtrationThe resulting suspension was filtered
  3. washthe solid was washed successively with water, ethyl acetate and diethyl ether
  4. customdried

Sources & evidence

ORD record
ord-73a06a556c304014a2b5668ca39ac412
Source dataset
uspto-grants-2008_07
Patent number
US07402583B2

Reaction notes

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