Dimethylformamide → 2-Amino-1-naphthol

HRID 1867251Notes

Reaction equation

HRID 1867251 reaction equation
P([O:8][CH2:9][CH3:10])(OCC)OCC.N1[C:16]([CH3:17])=[CH:15][CH:14]=[CH:13][C:12]=1[CH3:18].C[N:20]([CH:22]=O)C>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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C(Cl)(Cl)Cl>[NH2:20][C:22]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:18][CH:12]=[CH:13][CH:14]=2)[C:9]=1[OH:8]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 79372,6-LutidineHCID 31215Triethyl phosphite

Product 1

HCID 390382-Amino-1-naphtholYield 82%

Reagents, catalysts & solvents 1

HCID 11029508Palladium, tris[mu-[(1,2-eta:4,5-eta)-(1E,4E)-1,5-diphenyl-1,4-pentadien-3-one]]di-, compd. with trichloromethane (1:1)Catalyst

Procedure

To dry DMF (60 mL) were added Pd2 dba3-CHCl3 (0.04 g, 0.038 mmol), and triethyl phosphite (0.04 mL, 0.229 mmol), and the solution was aged for 5 minutes at room temperature. The mixture was degassed with 3 nitrogen/vacuum cycles and stirred for 30 minutes until solution became yellow. Then the naphtholamine 145 (0.20 g, 0.80 mmol), CPI 5 (0.52 g, 0.88 mmol), and 2,6-lutidine (0.046 mL, 0.4 mmole) were added to the reaction solution and the resulting mixture was aged for 3 hours. Solvent was removed under reduced pressure and crude residue was purified by flash column chromatography with 97:3 CH2Cl2/MeOH to afford the desired couple product 146 as a yellow oil (0.47 g, 82% yield).

Workup

  1. customThe mixture was degassed with 3 nitrogen/vacuum cycles
  2. waitthe resulting mixture was aged for 3 hours
  3. customSolvent was removed under reduced pressure and crude residue
  4. customwas purified by flash column chromatography with 97:3 CH2Cl2/MeOH

Sources & evidence

ORD record
ord-94056e1eaca740c1924cae2a02bef98c
Source dataset
uspto-grants-2009_12
Patent number
US07632828B2

Reaction notes

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