Sodium Hydroxide → HCID 18470635, compound

HRID 1004012Notes

Reaction equation

HRID 1004012 reaction equation
S(S([O-])=O)([O-])=O.[Na+].[Na+].[CH:9]1([O:13][C:14]2[C:23]([O:24][CH3:25])=[C:22]([O:26][CH3:27])[CH:21]=[C:20]([N+:28]([O-])=O)[C:15]=2[C:16]([O:18][CH3:19])=[O:17])[CH2:12][CH2:11][CH2:10]1.[OH-].[Na+]>O.[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl>[NH2:28][C:20]1[C:15]([C:16]([O:18][CH3:19])=[O:17])=[C:14]([O:13][CH:9]2[CH2:12][CH2:11][CH2:10]2)[C:23]([O:24][CH3:25])=[C:22]([O:26][CH3:27])[CH:21]=1

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 24489Sodium DithioniteHCID 18470625HCID 18470625, compound

Product 1

HCID 18470635HCID 18470635, compoundYield 108.4%

Reagents, catalysts & solvents 3

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of sodium dithionite (3 g, 0.017 mol) in water (6 ml) was added to a solution of methyl 2-cyclobutyloxy-3,4-dimethoxy-6-nitrobenzoate (511 mg, 0.00164 mol) and tetra-n-butylammonium chloride (280 mg, 0.001 mol) in dichloromethane (15 ml) and the reaction stirred vigorously for 1 hour at room temperature. The mixture was basified with 2N aqueous sodium hydroxide solution (10 ml) and extracted with dichloromethane (3×20 ml). The combined organic extracts were washed with water (30 ml), dried (MgSO4), filtered and evaporated under reduced pressure. The residue was dissolved in a minimum volume of dichloromethane and an excess of ethereal hydrogen chloride added. The resulting precipitate was filtered and partitioned between saturated aqueous sodium bicarbonate solution and dichloromethane. The organic layer was evaporated under reduced pressure to give the subtitle compound (500 mg). Rf 0.70 (diethyl ether). 1H-NMR (CDCl3): δ=1.46 (1H, m), 1.70 (1H, m), 2.28 (4H, m), 3.72 (3H, s), 3.83 (3H, s), 3.90 (3H, s), 4.52 (1H, m), 5.20 (2H, bs), 5.82 (1H, s).

Workup

  1. extractionextracted with dichloromethane (3×20 ml)
  2. washThe combined organic extracts were washed with water (30 ml)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. dissolutionThe residue was dissolved in a minimum volume of dichloromethane
  7. additionan excess of ethereal hydrogen chloride added
  8. filtrationThe resulting precipitate was filtered
  9. custompartitioned between saturated aqueous sodium bicarbonate solution and dichloromethane
  10. customThe organic layer was evaporated under reduced pressure

Sources & evidence

ORD record
ord-97b85526f52742f7820854eb5a247a0f
Source dataset
uspto-grants-2000_04
Patent number
US06048864

Reaction notes

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