Triphenylphosphine → HCID 67255056, compound

HRID 1830737Notes

Reaction equation

HRID 1830737 reaction equation
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[C:6]([OH:13])[CH:5]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:34][N:35]([CH3:40])[CH2:36][CH2:37][CH2:38]O.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1.Cl>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[C:6]([O:13][CH2:38][CH2:37][CH2:36][N:35]([CH3:40])[CH3:34])[CH:5]=1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 766463-(Dimethylamino)-1-propanolHCID 294866Methyl 3-hydroxy-4-nitrobenzoate

Product 1

HCID 67255056HCID 67255056, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred, cooled (about 0° C.) solution of 3-hydroxy-4-nitro benzoic acid methyl ester. (394 mg, 2.0 mmol), triphenyl phosphine (525 mg, 2.0 mmol), arid 3-(dimethylamino)-propanol (237 μL, 2.0 mmol) in dry tetrahydrofuran (5 mL) was added diisopropyl azodicarboxylate (394 μL, 2.0 mmol in 1 mL of tetrahydrofuran). After stirring for 12 hours, the reaction was diluted with hydrochloric acid (30 mL of a 1M solution) and extracted with ethyl acetate (2×50 mL). The aqueous solution was basified with 10% aqueous sodium carbonate (50 mL) and the product was extracted with ethyl acetate (3×100 mL). The ethyl acetate was washed with brine (1×30 mL), then dried (MgSO4), and filtered. The filtered solution was concentrated under reduced pressure to provide the desired crude product (86% yield). 1H-NMR (400 MHz, CDCl3) δ7.81 (d, 1H), 7.78 (s, 1H), 7.65 (d, 1H, 4.23 (t, 2H), 3.91 (s, 3H),2.44 (t, 2H), 2.22 (s, 6H), 2.05 (m, 2H).

Workup

  1. extractionextracted with ethyl acetate (2×50 mL)
  2. extractionthe product was extracted with ethyl acetate (3×100 mL)
  3. washThe ethyl acetate was washed with brine (1×30 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationThe filtered solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-b842b2def7f845d0a016479deeea0b60
Source dataset
uspto-grants-2006_06
Patent number
US07067506B2

Reaction notes

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