Hydrochloric Acid → HCID 59443444, compound

HRID 1035625Notes

Reaction equation

HRID 1035625 reaction equation
[CH3:1][O:2][C:3]1[C:4]([C:21](O)=[O:22])=[CH:5][C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[C:8]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=1)[CH:7]=2.CCN=C=NCCCN(C)C.O[C:36]1[C:44]2[N:43]=NN[C:40]=2[CH:39]=[CH:38][CH:37]=1.NC1C=CC=CC=1.C(N(CC)CC)C.Cl>ClCCl>[CH3:1][O:2][C:3]1[C:4]([C:21]([NH:43][C:44]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)=[O:22])=[CH:5][C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[C:8]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=1)[CH:7]=2

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 6115AnilineHCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 59443490HCID 59443490, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 59443444HCID 59443444, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

3-Methoxy-7-(3-methoxyphenyl)-2-naphthoic acid (323 mg, 1.05 mmol, 1 eq), EDCI (1 eq) and hydroxybenzotriazole (1 eq) are dissolved in 50 ml of dry dichloromethane. To this solution, cooled at 0° C., are added dropwise aniline (1 eq) and triethylamine (1 eq) in 40 ml of dry dichloromethane. The reaction mixture is boiled under reflux for 1.5 h, and after cooling, the reaction is stopped by adding 20 ml of 0.1 M HCl. The organic phase is separated, washed with saturated sodium carbonate and chloride solutions, dried over magnesium sulfate, filtered and concentrated in vacuum on a rotary evaporator. Purification by column chromatography with hexane/ethyl acetate 8/2 and 6/4 as the eluent yielded the desired product in a yield of 70%, 282 mg.

Workup

  1. temperatureunder reflux for 1.5 h
  2. temperatureafter cooling
  3. customThe organic phase is separated
  4. washwashed with saturated sodium carbonate and chloride solutions
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuum on a rotary evaporator
  8. customPurification by column chromatography with hexane/ethyl acetate 8/2 and 6/4 as the eluent

Sources & evidence

ORD record
ord-218e28264bcd477099b270a1dc408d7d
Source dataset
uspto-grants-2013_10
Patent number
US08546392B2

Reaction notes

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