Hydrochloric Acid → N-(4-Carboxybenzyl)-(2-naphthoxy)acetamide

HRID 359660

Reaction equation

HRID 359660 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[O:11][CH2:12][C:13]([OH:15])=O.C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:28][CH2:29][C:30]1[CH:35]=[CH:34][C:33]([C:36]([OH:38])=[O:37])=[CH:32][CH:31]=1.Cl[Si](C)(C)C.Cl>C(Cl)Cl.C(N(CC)CC)C>[C:36]([C:33]1[CH:34]=[CH:35][C:30]([CH2:29][NH:28][C:13](=[O:15])[CH2:12][O:11][C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH:1]=2)=[CH:31][CH:32]=1)([OH:38])=[O:37]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 6397ChlorotrimethylsilaneHCID 84222-Naphthoxyacetic acidHCID 655264-(Aminomethyl)Benzoic AcidHCID 682631,1'-Carbonyldiimidazole

Product 1

HCID 13922246N-(4-Carboxybenzyl)-(2-naphthoxy)acetamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

(2-Naphthoxy)acetic acid (8.5 g) is suspended in 160 mL methylene chloride and treated with 1,1'-carbonyldiimidazole (6.8 g) which is added in small portions. After stirring for 3 hrs at room temperature under a nitrogen atmosphere, the mixture is added dropwise to a previously prepared solution of alpha-amino-p-toluic acid (1.4 g), chlorotrimethylsilane (10 mL), and triethylamine (11 mL) in 250 mL methylene chloride at 0° C. The final mixture is stirred at room temperature under a nitrogen atmosphere overnight. The mixture is combined with 200 mL 1 N HCl and shaken, after which the resultant precipitate is collected by suction filtration. The precipitate is recrystallized from methanol/2N HCl, m.p. 188°-189° C. as N-(4-carboxybenzyl)-(2-naphthoxy)acetamide.

Workup

  1. additionis added in small portions
  2. stirringshaken
  3. filtrationafter which the resultant precipitate is collected by suction filtration
  4. customThe precipitate is recrystallized from methanol/2N HCl, m.p. 188°-189° C. as N-(4-carboxybenzyl)-(2-naphthoxy)acetamide

Sources & evidence

ORD record
ord-0aa585abb3e4471a82cf99f8e131bd05
Source dataset
uspto-grants-1991_03
Patent number
US05002703

Linked notes

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