2-Methyl-1-naphthylamine → HCID 58114881, compound

HRID 2266931Notes

Reaction equation

HRID 2266931 reaction equation
Br[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]1[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=[CH:14][CH:13]=1)[CH:8]=[CH:7]2.[CH3:22][C:23]1[CH:32]=[CH:31][C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:24]=1[NH2:33].C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2N(C)C)CCCCC1.CC([O-])(C)C.[Na+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].O.C1(C)C=CC=CC=1>[CH3:22][C:23]1[CH:32]=[CH:31][C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:24]=1[NH:33][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]1[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=[CH:14][CH:13]=1)[CH:8]=[CH:7]2

Participants

8

Reactant 4

HCID 167332-Methyl-1-naphthylamineHCID 27342172-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenylHCID 23676156Sodium t-butoxideHCID 58114889HCID 58114889, compound

Product 1

HCID 58114881HCID 58114881, compound

Reagents, catalysts & solvents 3

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 8-bromo-2-(1-naphthyl)quinoline (3.25 g, 9.7 mmol), 2-methyl-1-naphthalenamine (1.76 g, 11.2 mmol), Pd(dba)2 (0.12 g, 0.2 mmol), L=(N-[2′-(dicyclohexylphosphino)[1,1′-biphenyl]-2-yl]-N,N-dimethylamine (0.15 g, 0.4 mmol), NaOtBu (1.15 g, 12 mmol) and toluene (20 mL) is stirred for 8 h under an argon atmosphere at 100° C. in oil bath. The mixture is then poured into water and extracted with benzene (3×40 mL). The combined organic phases are washed with water and brine and then concentrated. The residue is purified by column chromatography (silica gel 40, hexane/toluene 4:1). Yield 3.1 g (78%).

Workup

  1. extractionextracted with benzene (3×40 mL)
  2. washThe combined organic phases are washed with water and brine
  3. concentrationconcentrated
  4. customThe residue is purified by column chromatography (silica gel 40, hexane/toluene 4:1)

Sources & evidence

ORD record
ord-ccdbbac95b574b1db30858ebee76c074
Source dataset
uspto-grants-2010_12
Patent number
US07858718B1

Reaction notes

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