Triphenylphosphine → 2-Amino-4-((4-nitronaphthalen-1-yloxy)methyl)pyridine

HRID 2067000Notes

Reaction equation

HRID 2067000 reaction equation
[N+:1]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([OH:14])=[CH:6][CH:5]=1)([O-:3])=[O:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[NH2:34][C:35]1[CH:40]=[C:39]([CH2:41]O)[CH:38]=[CH:37][N:36]=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[NH2:34][C:35]1[CH:40]=[C:39]([CH2:41][O:14][C:7]2[C:8]3[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[CH:38]=[CH:37][N:36]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 3438294-Nitro-1-naphtholHCID 1515296(2-Aminopyridin-4-yl)methanol

Product 1

HCID 584167602-Amino-4-((4-nitronaphthalen-1-yloxy)methyl)pyridineYield 56.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-nitronaphthol (5.17 g, 27.3 mmol), triphenylphosphine (10.75 g, 41.0 mmol) and 2-aminopyridine-4-methanol (2) (5.09 g, 41.0 mmol) in THF (50 mL), at −15° C., was added dropwise diisopropyl azodicarboxylate (DIAD) (8.07 mL, 41.0 mmol). The mixture was stirred overnight at RT and the volatiles then removed in vacuo. The crude product was triturated from EtOAc (150 mL), filtered off and washed with EtOAc (100 mL). A second trituration from MeOH (100 mL) gave 2-amino-4-[(4-nitronaphthalen-1-yloxy)methyl]pyridine (3) (4.54 g, 56%) as a yellow solid: m/z 296 (M+H)+ (ES+).

Workup

  1. customthe volatiles then removed in vacuo
  2. customThe crude product was triturated from EtOAc (150 mL)
  3. filtrationfiltered off
  4. washwashed with EtOAc (100 mL)

Sources & evidence

ORD record
ord-8f1438e8a2ea406fbe0e649bcf4c417b
Source dataset
uspto-grants-2012_10
Patent number
US08293771B2

Reaction notes

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