Water → 1-hydroxy-4-ethoxy-carbonylmethyloxy-N-(3-n-dodecyloxypropyl)-2-naphthamide

HRID 2166913Notes

Reaction equation

HRID 2166913 reaction equation
[N+](C1C=CC(O[C:11]([C:13]2[CH:22]=[C:21]([O:23][CH2:24][C:25](OCC)=O)[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]=2[OH:30])=[O:12])=CC=1)([O-])=O.[CH2:31]([O:43][CH2:44][CH2:45][CH2:46][NH2:47])[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42].[O:48]1[CH2:52][CH2:51]CC1.[OH2:53]>C(OCC)(=O)C>[OH:30][C:14]1[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:21]([O:23][CH2:24][CH3:25])=[C:22]([O:53][CH:51]=[C:52]=[O:48])[C:13]=1[C:11]([NH:47][CH2:46][CH2:45][CH2:44][O:43][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])=[O:12]

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 655963-(Dodecyloxy)propylamineHCID 3335330HCID 3335330, compound

Product 1

HCID 867389361-hydroxy-4-ethoxy-carbonylmethyloxy-N-(3-n-dodecyloxypropyl)-2-naphthamideYield 66%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

271 g (0.66 mol) of 1-hydroxy-4-ethoxycarbonylmethyloxy-2-naphthoic acid 4-nitrophenyl ester and 160 g (0.66 mol) of 3-n-dodecyloxypropylamine were added to 750 ml of tetrahydrofuran, and the mixture was stirred for 3 hours. 2 liters of water were added to the reacting solution, and extraction was carried out with 1 liter of ethyl acetate. After removal of ethyl acetate by distillation, the residue was dissolved in 1 liter of methanol, and cooled. The precipitated crystals were filtered off and dried to obtain 205 g (66% yield) of 1 -hydroxy-4-ethoxy-carbonylmethyloxy-N-(3-n-dodecyloxypropyl)-2-naphthamide. Melting point: 66°-67.5° C.

Workup

  1. customAfter removal of ethyl acetate
  2. distillationby distillation
  3. dissolutionthe residue was dissolved in 1 liter of methanol
  4. temperaturecooled
  5. filtrationThe precipitated crystals were filtered off
  6. customdried

Sources & evidence

ORD record
ord-3068c7bf88d54774b8b2fc15daf193c9
Source dataset
uspto-grants-1983_06
Patent number
US04390618

Reaction notes

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