3'-Acetamido-2-bromoacetophenone → 4-(6,8-Dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)aniline

HRID 1295427Notes

Reaction equation

HRID 1295427 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Cl:12])[CH:11]=1)[CH2:8][N:7]([CH3:13])[CH2:6][CH:5]2[C:14]1[CH:19]=[CH:18][C:17]([C@@](O)([C@@H](O)[C@H](O)[C@H](O)CO)C(N)=O)=[CH:16][CH:15]=1.BrCC(C1C=C([NH:43]C(=O)C)C=CC=1)=O>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Cl:12])[CH:11]=1)[CH2:8][N:7]([CH3:13])[CH2:6][CH:5]2[C:14]1[CH:19]=[CH:18][C:17]([NH2:43])=[CH:16][CH:15]=1

Participants

3

Reactant 2

HCID 124318473'-Acetamido-2-bromoacetophenone2×HCID 69511913[4-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)phenyl]-(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanamide2×

Product 1

HCID 99443944-(6,8-Dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)aniline

Procedure

Starting from 2,4-dichlorobenzylmethylamine (Example 1, intermediate 1) and N-[3-(2-bromoacetyl)phenyl]acetamide (cf. Example 1, intermediate 2), the aniline derivative 3-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)phenylamine (cf. Example 1, intermediate 6) was prepared in a similar manner to the synthetic route described in Example 1.

Sources & evidence

ORD record
ord-49cc90ade7cd4173844a4f99eb7db0dd
Source dataset
uspto-grants-2007_07
Patent number
US07241775B2

Reaction notes

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