Ethanol → HCID 59464277, compound

HRID 1713817Notes

Reaction equation

HRID 1713817 reaction equation
O.O.[Sn](Cl)Cl.[N:6]1([C:12]2[CH:23]=[CH:22][C:21]([N+:24]([O-])=O)=[CH:20][C:13]=2[C:14]([O:16][CH2:17][CH:18]=[CH2:19])=[O:15])[CH2:11][CH2:10][O:9][CH2:8][CH2:7]1.C(O)C>CCOC(C)=O>[NH2:24][C:21]1[CH:22]=[CH:23][C:12]([N:6]2[CH2:7][CH2:8][O:9][CH2:10][CH2:11]2)=[C:13]([CH:20]=1)[C:14]([O:16][CH2:17][CH:18]=[CH2:19])=[O:15]

Participants

5

Reactant 3

HCID 702EthanolHCID 61436Stannous chloride dihydrate2×HCID 59464172HCID 59464172, compound

Product 1

HCID 59464277HCID 59464277, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Tin(II) chloride dihydrate (17.37 g, 77 mmol) was added to a solution of allyl 2-morpholin-4-yl-5-nitrobenzoate (11.24 g, 38.5 mmol) in EtOAc (250 mL) and the mixture was stirred and heated under reflux for 4 h. Ethanol (150 mL) was added, followed by another portion of Tin(II) chloride dihydrate (17.4 g) and the mixture was heated for another 2 h. The mixture was cooled and filtered then the filtrate was washed repeatedly with aqueous ammonium hydroxide and re-filtered. The organic layer was dried and concentrated by evaporation to give the title compound (Intermediate 76, 5.42 g, 54%) as a solid; 1H NMR δ 6.90 (1H, d), 6.80 (1H, s), 6.70 (1H, d), 6.10-5.95 (1H, m), 5.40 (1H, d), 5.30 (1H, d), 5.00 (2H, s), 4.80 (2H, s), 3.70-3.60 (4H, m), 3.20-3.10 (4H, m); MS m/e MH+ 263.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 4 h
  3. temperaturethe mixture was heated for another 2 h
  4. temperatureThe mixture was cooled
  5. filtrationfiltered
  6. washthe filtrate was washed repeatedly with aqueous ammonium hydroxide
  7. filtrationre-filtered
  8. customThe organic layer was dried
  9. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-0b9fca07093643bc8c390356b32c50d8
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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