Water → HCID 3149442, compound

HRID 1158596Notes

Reaction equation

HRID 1158596 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[C:7]([OH:12])[CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1.[N+:13]([C:16]1[CH:24]=[CH:23][C:19]([C:20](Cl)=[O:21])=[CH:18][CH:17]=1)([O-:15])=[O:14].[OH2:25]>N1C=CC=CC=1.CN(C1C=CN=CC=1)C>[N+:13]([C:16]1[CH:24]=[CH:23][C:19]([C:20]([O:1][C:2]2[C:11]3[C:6](=[C:7]([O:12][C:20](=[O:21])[C:19]4[CH:23]=[CH:24][C:16]([N+:13]([O-:14])=[O:25])=[CH:17][CH:18]=4)[CH:8]=[CH:9][CH:10]=3)[CH:5]=[CH:4][CH:3]=2)=[O:21])=[CH:18][CH:17]=1)([O-:15])=[O:14]

Participants

6

Reactant 3

HCID 962WaterHCID 67491,5-DihydroxynaphthaleneHCID 85024-Nitrobenzoyl chloride

Product 1

HCID 3149442HCID 3149442, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

8.0 g of 1,5-dihydroxynaphtalene (50.0 mM) were dissolved in 150 ml of pyridine and the solution was cooled to 0° C. At this temperature were added portionwise 27.8 g of 4-nitrobenzoylchloride (150.0 mM), whereupon the temperature rose to Ca. 30° C. Then, 0.6 g of DMAP (5.0 mM) were added and the mixture was stirred overnight at 140° C. bath-temperature. The next day, the reaction mixture was allowed to cool to room temperature and 500 ml of water were added and the resulting mixture was stirred for 1 h at 140° C. bath-temperature. It was then cooled to room temperature and filtered. The cake was washed with water and dried to give 22.2 9 (48.4 mM, 97%) of 5-[(4-nitrobenzoyl)oxy]-1-naphthyl 4-nitrobenzoate as beige crystals.

Workup

  1. custom30° C
  2. temperatureto cool to room temperature
  3. stirringthe resulting mixture was stirred for 1 h at 140° C. bath-temperature
  4. temperatureIt was then cooled to room temperature
  5. filtrationfiltered
  6. washThe cake was washed with water
  7. customdried

Sources & evidence

ORD record
ord-7bf4648b86104878b44865185d8a5ca2
Source dataset
uspto-grants-2010_10
Patent number
US07811642B2

Reaction notes

Loading…