Ethanol → HCID 68802648, compound

HRID 1270760Notes

Reaction equation

HRID 1270760 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7](C(O)=O)[CH:6]=[CH:5]2.C([N:17]([CH2:20]C)CC)C.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:29])=CC=1.[CH2:39]([OH:41])[CH3:40]>O1CCOCC1>[CH2:39]([O:41][C:20](=[O:29])[NH:17][C:7]1[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([OH:1])[CH:3]=2)[CH:8]=1)[CH3:40]

Participants

6

Reactant 4

HCID 702EthanolHCID 8471TriethylamineHCID 855576-Hydroxy-2-naphthoic acidHCID 199401P,P-Diphenylphosphinic azide

Product 1

HCID 68802648HCID 68802648, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a suspension of 6-hydroxy-2-naphthoic acid (5 g, 26.6 mmol) and triethylamine (7.39 mL, 53.1 mmol) in 1,4-dioxane (50 mL) at room temperature, is added DPPA (8.59 mL, 39.9 mmol). After stirring at room temperature for 2.5 hours, ethanol (15.5 mL, 266 mmol) is added and the reaction is heated to reflux temperature overnight. After cooling to room temperature, the mixture is partitioned between EtOAc and water. The organic layer is washed with brine, dried (Na2SO4) and concentrated by rotary evaporator to give an oil. Flash chromatography on silica gel (5% methanol in dichloromethane) gives N-(6-hydroxy-2-naphthyl)carbamic acid ethyl ester as a white solid.

Workup

  1. temperaturethe reaction is heated
  2. temperatureto reflux temperature overnight
  3. temperatureAfter cooling to room temperature
  4. customthe mixture is partitioned between EtOAc and water
  5. washThe organic layer is washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated by rotary evaporator
  8. customto give an oil

Sources & evidence

ORD record
ord-59947d7c0b85480d937c702a8a0deae0
Source dataset
uspto-grants-2007_04
Patent number
US07202364B2

Reaction notes

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