Acetic Acid → 4-(4-Aminonaphthalen-1-yloxy)pyridin-2-amine

HRID 2069115Notes

Reaction equation

HRID 2069115 reaction equation
[N+:1]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([O:14][C:15]2[CH:20]=[CH:19][N:18]=[C:17]([NH2:21])[CH:16]=2)=[CH:6][CH:5]=1)([O-])=O.C(Cl)Cl.C(O)(=O)C.[H][H]>CO.[Pt]>[NH2:1][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([O:14][C:15]2[CH:20]=[CH:19][N:18]=[C:17]([NH2:21])[CH:16]=2)=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 6344DichloromethaneHCID 585325624-(4-Nitronaphthalen-1-yloxy)pyridin-2-amineHCID 178418361HCID 178418361, compound

Product 1

HCID 585325554-(4-Aminonaphthalen-1-yloxy)pyridin-2-amine

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 887MethanolSolvent

Procedure

A solution of 4-(4-nitronaphthalen-1-yloxy)pyridin-2-amine (2.00 g, 7.11 mmol) in a mixture of methanol (70 mL), DCM (70 mL) and acetic acid (5 mL) was subjected to hydrogenation by passage through a Thales H-cube (1.0 mL min−1, RT, 55 mm 10% Pt/C Cat-Cart, full hydrogen mode) and was then evaporated in vacuo. The residue was taken up into DCM (100 mL), and was washed with sat. NaHCO3 (100 mL) and brine (100 mL) and then dried (MgSO4) and evaporated in vacuo. The crude product was purified by flash column chromatography (SiO2, 80 g, EtOAc in isohexane, 20 to 80%, gradient elution) to afford the title compound, Intermediate E as a brown solid (1.70 g, 85%); Rt 1.04 min (Method 2); m/z 252 (M+H)+ (ES+).

Workup

  1. customwas then evaporated in vacuo
  2. washwas washed with sat. NaHCO3 (100 mL) and brine (100 mL)
  3. dry with materialdried (MgSO4)
  4. customevaporated in vacuo
  5. customThe crude product was purified by flash column chromatography (SiO2, 80 g, EtOAc in isohexane, 20 to 80%, gradient elution)

Sources & evidence

ORD record
ord-947ecb245bff4cc5820c7c1394756a14
Source dataset
uspto-grants-2012_10
Patent number
US08299074B2

Reaction notes

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