Monomethyl terephthalate → 2-(4-Methoxycarbonylbenzamido)-4'-methoxyacetophenone

HRID 2270050Notes

Reaction equation

HRID 2270050 reaction equation
Cl.[NH2:2][CH2:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][CH:7]=1)=[O:5].[CH3:14][O:15][C:16](=[O:26])[C:17]1[CH:25]=[CH:24][C:20]([C:21](O)=[O:22])=[CH:19][CH:18]=1>N1C=CC=CC=1.C(N(CC)CC)C.ClCCl>[CH3:14][O:15][C:16]([C:17]1[CH:25]=[CH:24][C:20]([C:21]([NH:2][CH2:3][C:4]([C:6]2[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][CH:7]=2)=[O:5])=[O:22])=[CH:19][CH:18]=1)=[O:26]

Participants

6

Reactant 2

HCID 15513Monomethyl terephthalateHCID 124871882-Amino-4'-methoxyacetophenone hydrochloride

Product 1

HCID 136403692-(4-Methoxycarbonylbenzamido)-4'-methoxyacetophenoneYield 92.1%

Reagents, catalysts & solvents 3

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent3×HCID 8471TriethylamineSolvent

Procedure

To a solution of 2-amino-4′-methoxyacetophenone hydrochloride (5.33 g) in pyridine (4.28 ml), triethylamine (3.68 ml) and dichloromethane (50 ml) was added dropwise a solution of terephthalic acid monomethyl ester (5.25 g) in dichloromethane (10 ml) at 0° C. The reaction mixture was allowed to warm to room temperature, and stirred for 3 hours. To the reaction mixture was added dichloromethane (200 ml), washed with 1N-sodium hydroxide (100 ml×2), saturated hydrogen carbonate aqueous solution (100 ml×2) and brine, and dried over magnesium sulfate. Magnesium sulfate was filtered off, and the filtrate was evaporated under reduced pressure. The solids were slurried in n-hexane, and collected by filtration to give 2-(4-methoxycarbonyl-benzamido)-4′-methoxyacetophenone (7.97 g).

Workup

  1. washwashed with 1N-sodium hydroxide (100 ml×2), saturated hydrogen carbonate aqueous solution (100 ml×2) and brine
  2. dry with materialdried over magnesium sulfate
  3. filtrationMagnesium sulfate was filtered off
  4. customthe filtrate was evaporated under reduced pressure
  5. filtrationcollected by filtration

Sources & evidence

ORD record
ord-6166f9853aa6469cbc73aef21e32c70a
Source dataset
uspto-grants-2001_12
Patent number
US06331521B1

Reaction notes

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