Phenylboronic Acid → 5-Acetamido-2-methyl-6-nitro-8-phenyl-1,2,3,4-tetrahydro-isoquinoline

HRID 1417042Notes

Reaction equation

HRID 1417042 reaction equation
[CH3:1][N:2]1[CH2:11][CH2:10][C:9]2[C:4](=[C:5]([N+:18]([O-:20])=[O:19])[CH:6]=[CH:7][C:8]=2C2C=CC=CC=2)[CH2:3]1.[C:21]1(B(O)O)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.BrC1C=CC([N+]([O-])=O)=C2C=1[CH2:33][CH2:34][N:35](C)C2.CN1CCC2C(=C([N+]([O-])=[O:64])C=CC=2C2C=CC(Cl)=CC=2)C1>>[C:34]([NH:35][C:4]1[C:5]([N+:18]([O-:20])=[O:19])=[CH:6][C:7]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[C:8]2[C:9]=1[CH2:10][CH2:11][N:2]([CH3:1])[CH2:3]2)(=[O:64])[CH3:33]

Participants

5

Reactant 4

HCID 66827Phenylboronic AcidHCID 100160105-Bromo-2-methyl-8-nitro-1,2,3,4-tetrahydroisoquinolineHCID 234358215-(4-Chlorophenyl)-N-methyl-8-nitro-1,2,3,4-tetrahydroisoquinolineHCID 234358582-Methyl-5-phenyl-8-nitro-1,2,3,4-tetrahydro-isoquinoline

Product 1

HCID 234358595-Acetamido-2-methyl-6-nitro-8-phenyl-1,2,3,4-tetrahydro-isoquinoline

Procedure

2-methyl-5-phenyl-8-nitro-1,2,3,4-tetrahydro-isoquinoline mp 75-78° C. from reaction between phenyl boronic acid and 5-bromo-2-methyl-8-nitro-1,2,3,4-tetrahydro-isoquinoline. 2-methyl-5-(4-chlorophenyl)-8-nitro-1,2,3,4-tetrahydro-isoquinoline mp 162-163° C.

Sources & evidence

ORD record
ord-6da1b13d12dc4441add099efb4d7deaa
Source dataset
uspto-grants-1999_06
Patent number
US05917053

Reaction notes

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