Ammonia → 4-[[2-(2-Naphthalenyloxy)ethyl]oxy]-alpha-oxobenzeneacetamide

HRID 2225756Notes

Reaction equation

HRID 2225756 reaction equation
C[O:2][C:3](=O)[C:4](=[O:25])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][O:14][C:15]2[CH:24]=[CH:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=2)=[CH:7][CH:6]=1.[NH3:27]>CO.O1CCCC1>[CH:16]1[C:17]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:23]=[CH:24][C:15]=1[O:14][CH2:13][CH2:12][O:11][C:8]1[CH:9]=[CH:10][C:5]([C:4](=[O:25])[C:3]([NH2:27])=[O:2])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 541704664-[2-(2-Naphthalenyloxy)ethoxy]-alpha-oxobenzeneacetic acid methyl ester

Product 1

HCID 190043044-[[2-(2-Naphthalenyloxy)ethyl]oxy]-alpha-oxobenzeneacetamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-[[2-(2-naphthalenyloxy)ethyl]oxy]-alpha-oxobenzeneacetic acid methyl ester (0.5 g) in methanol (40 mL) and tetrahydrofuran (40 mL) was chilled in an ice bath and saturated with ammonia gas. The cooling bath was removed and the mixture was stirred at room temperature for 4 hours and the solution was evaporated to dryness. Crystallization from tetrahydrofuran-ethyl alcohol provided 0.4 g of 4-[[2-(2-naphthalenyloxy)ethyl]oxy]-alpha-oxobenzeneacetamide as a colorless solid, mp 194°-196° C.

Workup

  1. customThe cooling bath was removed
  2. customthe solution was evaporated to dryness
  3. customCrystallization from tetrahydrofuran-ethyl alcohol

Sources & evidence

ORD record
ord-814f82024351432ea74d0d455c2da9e9
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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