Malonic Acid → 2,4-Dichloro-7-methoxy-8-methylquinoline

HRID 530725Notes

Reaction equation

HRID 530725 reaction equation
Cl.[CH3:2][C:3]1[C:9]([O:10][CH3:11])=[CH:8][CH:7]=[CH:6][C:4]=1[NH2:5].C(O)(=O)CC(O)=O.[Cl:19][C:20]1[CH:29]=[C:28]([Cl:30])C2C(=C(Cl)C(OC)=CC=2)N=1>>[Cl:19][C:20]1[CH:29]=[C:28]([Cl:30])[C:6]2[C:4](=[C:3]([CH3:2])[C:9]([O:10][CH3:11])=[CH:8][CH:7]=2)[N:5]=1

Participants

4

Reactant 3

HCID 867Malonic AcidHCID 27945162,4,8-Trichloro-7-methoxyquinolineHCID 529111383-Methoxy-2-methylaniline hydrochloride

Product 1

HCID 534009542,4-Dichloro-7-methoxy-8-methylquinolineYield 43%

Procedure

Compound 220b was synthesized from 2-methyl-3-methoxyaniline hydrochloride 215b and malonic acid as a white powder in 43% yield, following the procedure as described for compound 220d. 1H NMR (CDCl3, 376 MHz) δ (ppm) 2.62 (s, 3H), 4.03 (s, 3H), 7.34 (s, 1H), 7.37 (d, J=9.02 Hz, 1H), 8.05 (d, J=9.02 Hz, 1H).

Sources & evidence

ORD record
ord-58d8018b60ca4faa94061339a251ec4b
Source dataset
uspto-grants-2016_05
Patent number
US09353100B2

Reaction notes

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