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

HRID 1774365Notes

Reaction equation

HRID 1774365 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.CC(OC(/N=N/C(OC(C)C)=O)=O)C>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 3438294-Nitro-1-naphtholHCID 1515296(2-Aminopyridin-4-yl)methanolHCID 5363146Diisopropyl azodicarboxylate

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 (5.09 g, 41.0 mmol) in THF (50 mL) at −15° C. was added dropwise DIAD (8.07 mL, 41.0 mmol) and the mixture then allowed to warm to RT and stirred overnight. The volatiles were removed in vacuo and the residue was triturated with EtOAc (150 mL), and the crude product was collected by filtration and washed with EtOAc (100 mL). A second trituration with MeOH (100 mL) gave 2-amino-4-((4-nitronaphthalen-1-yloxy)methyl)pyridine (4.54 g, 56%) as a yellow solid: m/z 296 (M+H)+ (ES+).

Workup

  1. customThe volatiles were removed in vacuo
  2. customthe residue was triturated with EtOAc (150 mL)
  3. filtrationthe crude product was collected by filtration
  4. washwashed with EtOAc (100 mL)

Sources & evidence

ORD record
ord-413e013a4bab4d039801cb5362d00638
Source dataset
uspto-grants-2016_02
Patent number
US09260410B2

Reaction notes

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