Hydrochloric Acid → Methyl [1-(2-((N,N-diphenylamino)carbamoyl)-1E-ethylidene)-1,2,3,4-tetrahydronaphthalen-5-yl]oxyacetate

HRID 234719

Reaction equation

HRID 234719 reaction equation
[C:1](/[CH:4]=[CH:5]/[CH:6]1[C:15]2[C:10](=[C:11]([O:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])[CH:12]=[CH:13][CH:14]=2)[CH2:9][CH2:8][CH2:7]1)([OH:3])=O.Cl.[C:23]1([N:29]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[NH2:30])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(N(CC)CC)C.Cl>C(Cl)Cl>[C:23]1([N:29]([NH:30][C:1]([CH2:4]/[CH:5]=[C:6]2\[CH2:7][CH2:8][CH2:9][C:10]3[C:15]\2=[CH:14][CH:13]=[CH:12][C:11]=3[O:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])=[O:3])[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 10738Hydrazine, 1,1-diphenyl-, hydrochloride (1:1)HCID 86750227Methyl [1-(2E-carboxyvinyl)-1,2,3,4-tetrahydronaphthalen-5-yl]oxyacetate

Product 1

HCID 86750228Methyl [1-(2-((N,N-diphenylamino)carbamoyl)-1E-ethylidene)-1,2,3,4-tetrahydronaphthalen-5-yl]oxyacetateYield 70.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of the carboxylic acid (prepared in reference example 5, 150 mg), 2-chloro-N-methylpyridinum iodide (197 mg). 1,1-diphenylhydrazine hydrochloride (147 mg) and triethylamine (0.216 ml) in methylene chloride (6 ml) was stirred overnight at room temperature. The mixture was poured into 1N hydrochloric acid, and extracted with methylene chloride. The extract was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, and evaporated. The residue was crystallized from crystallized ethyl acetate to give the title compound (as pale yellow powder; 167 mg) having the following physical data.

Workup

  1. extractionextracted with methylene chloride
  2. washThe extract was washed with a saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated
  5. customThe residue was crystallized
  6. customfrom crystallized ethyl acetate

Sources & evidence

ORD record
ord-0ffa1781a30545b6a46a0fe793fac147
Source dataset
uspto-grants-1997_01
Patent number
US05596009

Linked notes

Loading…