Triphenylphosphine → HCID 58416760, compound

HRID 872373

Reaction equation

HRID 872373 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].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=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 58416760HCID 58416760, compoundYield 56.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-nitronaphthol (5.17 g, 27.3 mmol), PPh3 (10.75 g, 41.0 mmol) and 2-aminopyridine-4-methanol (1) (5.09 g, 41.0 mmol) in THF (50 mL) was added dropwise DIAD (8.07 mL, 41.0 mmol) at −15° C. The mixture was stirred overnight at RT and the volatiles 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 (2) (4.54 g, 56%) as a yellow solid: m/z 296 (M+H)+ (ES+).

Workup

  1. customthe volatiles 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-d8d1cd533a6745e891573abf193f7bc9
Source dataset
uspto-grants-2015_03
Patent number
US08975285B2

Linked notes

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