Methanol → HCID 19906387, compound

HRID 2371794Notes

Reaction equation

HRID 2371794 reaction equation
C1(CC([NH:9][C:10]2[CH:19]=[C:18]3[C:13]([CH:14]=[CH:15][CH:16]=[C:17]3[CH2:20][C:21]3[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][C:22]=3[O:31][CH3:32])=[CH:12][CH:11]=2)=O)CCCC1.C1(C)C=CC(S(O)(=O)=O)=CC=1.CO>C(OCC)(=O)C>[NH2:9][C:10]1[CH:19]=[C:18]2[C:13]([CH:14]=[CH:15][CH:16]=[C:17]2[CH2:20][C:21]2[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][C:22]=2[O:31][CH3:32])=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 6101p-Toluenesulfonic acidHCID 21570391HCID 21570391, compound

Product 1

HCID 19906387HCID 19906387, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of methyl 4-[7-(cyclopentylacetamido)naphth-1-ylmethyl]-3-methoxybenzoate (15.00 g), anhydrous p-toluenesulfonic acid (11.97 g), and methanol (dried over 3A molecular sieves) (70 ml) was refluxed for 42 hours. After cooling, the mixture was added to ethyl acetate (250 ml), washed (saturated sodium bicarbonate, brine), dried (MgSO4) and evaporated. The solid obtained was recrystallized from 1:12 methanol:methylene chloride and petroleum ether to give methyl 4-(7-aminonaphth-1-ylmethyl)-3-methoxybenzoate (10.15 g, 91%) as a light tan solid; mp 138°-40° C., MS(CI), m/e=322(M+H).

Workup

  1. temperaturewas refluxed for 42 hours
  2. temperatureAfter cooling
  3. washwashed (saturated sodium bicarbonate, brine)
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe solid obtained
  7. customwas recrystallized from 1:12 methanol

Sources & evidence

ORD record
ord-5e10b6322517451ab5a70e1a16b36dd0
Source dataset
uspto-grants-1992_03
Patent number
US05095038

Reaction notes

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