Acetyl chloride → (S)-methyl 6-bromo-5-hydroxy-2-methyl-3,4-dihydroquinoline-1(2H)-carboxylate

HRID 1051564Notes

Reaction equation

HRID 1051564 reaction equation
[Br:1][C:2]1[C:3]([OH:16])=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:12](=[O:14])C)[C@@H:7]([CH3:15])[CH2:6][CH2:5]2.[C:17](Cl)(=[O:19])C.COC1C=CC=C2C=1CC[C@H](C)N2.BrC1C=CC2N(C(C3CC3)=O)[C@@H](C)CCC=2C=1O.C1(C(Cl)=O)CC1>>[Br:1][C:2]1[C:3]([OH:16])=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:12]([O:19][CH3:17])=[O:14])[C@@H:7]([CH3:15])[CH2:6][CH2:5]2

Participants

6

Reactant 5

HCID 6367Acetyl chlorideHCID 77637Cyclopropanecarbonyl chlorideHCID 118075405(S)-5-methoxy-2-methyl-1,2,3,4-tetrahydroquinolineHCID 118075679(S)-1-(6-bromo-5-hydroxy-2-methyl-3,4-dihydroquinolin-1(2H)-yl)ethanoneHCID 118075707(2S)-6-bromo-1-cyclopropanecarbonyl-2-methyl-1,2,3,4-tetrahydroquinolin-5-ol

Product 1

HCID 118076517(S)-methyl 6-bromo-5-hydroxy-2-methyl-3,4-dihydroquinoline-1(2H)-carboxylate

Procedure

Methyl (S)-6-bromo-5-hydroxy-2-methyl-3,4-dihydroquinoline-1(2H)-carboxylate was synthesized following the procedure for (5)-1-(6-bromo-5-hydroxy-2-methyl-3,4-dihydroquinolin-1(2H)-yl)ethanone substituting methyl chloroformate for acetyl chloride in Step 5 or from (2S)-5-methoxy-2-methyl-1,2,3,4-tetrahydroquinoline following the procedure used for the synthesis of (2S)-6-bromo-1-cyclopropanecarbonyl-2-methyl-1,2,3,4-tetrahydroquinolin-5-ol, substituting methyl chloroformate for cyclopropanecarbonyl chloride. MS: (ES, m/z): 300, 302 [M+H]+

Sources & evidence

ORD record
ord-b93733086f44495291cdb9868bd85cac
Source dataset
uspto-grants-2016_07
Patent number
US09388161B2

Reaction notes

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