2,4-Dichloro-7-methoxy-8-methylquinoline → 2-Chloro-8-methyl-7-methoxy-4-(4-methoxy-benzyloxy)-quinoline

HRID 388672Notes

Reaction equation

HRID 388672 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10](Cl)[C:9]2[C:4](=[C:5]([CH3:15])[C:6]([O:13][CH3:14])=[CH:7][CH:8]=2)[N:3]=1.ClC1C=C([O:27][CH2:28][C:29]2[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=2)C2C(=C(Cl)C(OC)=CC=2)N=1>>[Cl:1][C:2]1[CH:11]=[C:10]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=2)[C:9]2[C:4](=[C:5]([CH3:15])[C:6]([O:13][CH3:14])=[CH:7][CH:8]=2)[N:3]=1

Participants

3

Reactant 2

HCID 534009542,4-Dichloro-7-methoxy-8-methylquinolineHCID 566051532,8-Dichloro-7-methoxy-4-(4-methoxy-benzyloxy)-quinoline

Product 1

HCID 566051592-Chloro-8-methyl-7-methoxy-4-(4-methoxy-benzyloxy)-quinolineYield 50%

Procedure

2-Chloro-8-methyl-7-methoxy-4-(4-methoxy-benzyloxy)-quinoline 221b was synthesized from compound 220b as a white powder in 50% yield, following the procedure as described for compound 221d. 1H NMR (CDCl3, 376 MHz) δ (ppm) 2.60 (s, 3H), 3.85 (s, 3H), 3.97 (s, 3H), 5.18 (s, 2H), 6.69 (s, 1H), 6.97 (d, J=8.57 Hz, 1H), 7.19 (d, J=8.57 Hz, 1H), 7.42 (d, J=8.57 Hz, 1H), 8.02 (d, J=8.57 Hz, 1H).

Sources & evidence

ORD record
ord-6e03860b3d2147a7bb285b0650d1b092
Source dataset
uspto-grants-2013_02
Patent number
US08377962B2

Reaction notes

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