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Sodium Carbonate → 3-(6-Methoxynaphthalen-2-yl)aniline

HRID 240095
Notes
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Reaction equation

HRID 240095 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8](B(O)O)[CH:7]=[CH:6]2.Br[C:17]1[CH:18]=[C:19]([CH:21]=[CH:22][CH:23]=1)[NH2:20].C([O-])([O-])=O.[Na+].[Na+]>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([C:17]1[CH:18]=[C:19]([NH2:20])[CH:21]=[CH:22][CH:23]=1)[CH:7]=[CH:6]2
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 115623-BromoanilineHCID 46416926-Methoxy-2-naphthaleneboronic acid

Product 1

HCID 227240743-(6-Methoxynaphthalen-2-yl)anilineYield 75%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalyst
HCID 8071
1,2-Dimethoxyethane
Solvent

Procedure

6-methoxy-naphthalene-2-boronic acid (0.140 g, 0.693 mmol) and 3-bromoaniline (0.05 mL, 0.462 mmol) were combined in DME (2 mL) in a flame-dried, round-bottom flask. Na2CO3 (2M, 0.485 mL, 0.970 mmol) and Pd(PPh3)4 (0.017 g, 0.014 mmol) were added to the stirred solution. The reaction was refluxed overnight under argon flow, and subsequently cooled to room temperature. The solvent was removed under vacuum and the resulting residue was resuspended in H20 and extracted with CH2Cl2. The organic phase was dried over MgSO4 and concentrated under vacuum. The crude product was purified by silica column chromatography (0-20% EtOAc/hexanes). The purification was monitored by TLC. The solvent was removed under vacuum from fractions containing product, resulting in 0.06 g in 75% yield.

Workup

  1. temperatureThe reaction was refluxed overnight under argon flow
  2. customThe solvent was removed under vacuum
  3. extractionextracted with CH2Cl2
  4. dry with materialThe organic phase was dried over MgSO4
  5. concentrationconcentrated under vacuum
  6. customThe crude product was purified by silica column chromatography (0-20% EtOAc/hexanes)
  7. customThe purification
  8. customThe solvent was removed under vacuum from fractions
  9. additioncontaining product
  10. customresulting in 0.06 g in 75% yield

Sources & evidence

ORD record
ord-cd07075839e246c2aa00081e135a7be4
Source dataset
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08642788B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes