Water → (7-Hydroxy-naphthalen-1-yl)-carbamic acid phenyl ester

HRID 12408

Reaction equation

HRID 12408 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH:10]=[C:9]([OH:12])[CH:8]=[CH:7]2.Cl[C:14]([O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:15].C(=O)([O-])O.[Na+].O>ClCCl>[OH:12][C:9]1[CH:10]=[C:11]2[C:6]([CH:5]=[CH:4][CH:3]=[C:2]2[NH:1][C:14](=[O:15])[O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 83588-Amino-2-naphthalenolHCID 15891Phenyl chloroformateHCID 516892Sodium Bicarbonate

Product 1

HCID 20090380(7-Hydroxy-naphthalen-1-yl)-carbamic acid phenyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 8-amino-2-naphthol (100 mg) were added phenyl chloroformate (87 μl), saturated aqueous sodium hydrogen carbonate (0.5 ml), dichloromethane (1 ml) and water (0.5 ml), and the mixture was stirred for 3 hrs. The reaction mixture was diluted with dichloromethane. After washing with 1N hydrochloric acid, the organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated. Diethyl ether and hexane were added to the residue, and the precipitate was collected by filtration to give the title compound (160 mg). NMR data of Example 109: 1H-NMR (300 MHz, DMSO-d6) δ3.49 (2H, m), 4.06 (2H, s), 6.79 (4H, m), 7.10 (2H, m), 7.30 (2H, m), 7.75 (2H, m), 8.34 (1H, s), 9.69 (1H, s).

Workup

  1. washAfter washing with 1N hydrochloric acid
  2. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  3. customthe solvent was evaporated
  4. additionDiethyl ether and hexane were added to the residue
  5. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-f15264134eac4f0192cdd015c4b915cf
Source dataset
uspto-grants-2010_06
Patent number
US07728005B2

Linked notes

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