2,8-Dichloro-7-methoxy-4-(4-methoxy-benzyloxy)-quinoline → 2-Chloro-6-methoxy-4-(4-methoxybenzyloxy)-8-methyl-quinoline

HRID 925952Notes

Reaction equation

HRID 925952 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10](Cl)[C:9]2[C:4](=[C:5]([CH3:15])[CH:6]=[C:7]([O:13][CH3:14])[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])[CH:6]=[C:7]([O:13][CH3:14])[CH:8]=2)[N:3]=1

Participants

3

Reactant 2

HCID 566051532,8-Dichloro-7-methoxy-4-(4-methoxy-benzyloxy)-quinolineHCID 866277502,4-Dichloro-6-methoxy-8-methyl-quinoline

Product 1

HCID 866277512-Chloro-6-methoxy-4-(4-methoxybenzyloxy)-8-methyl-quinolineYield 58%

Procedure

2-Chloro-6-methoxy-4-(4-methoxybenzyloxy)-8-methyl-quinoline 221f was synthesized from compound 220f as a white solid in 58% yield, following the procedure as described for compound 221d. 1H NMR (CDCl3, 400 MHz) δ (ppm) 2.68 (s, 3H), 3.80 (s, 3H), 3.83 (s, 3H), 5.11 (s, 2H), 6.72 (s, 1H), 6.97 (d, J=9.03 Hz, 2H), 7.15 (dd, J=3.01 Hz and J=0.96 Hz, 1H), 7.20 (d, J=3.00 Hz, 1H), 7.40 (d, J=9.03 Hz, 2H).

Sources & evidence

ORD record
ord-345665ecc2214309bd7754378f8b0241
Source dataset
uspto-grants-2016_03
Patent number
US09284307B2

Reaction notes

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