4-Aminophenylacetic acid → HCID 17747304, compound

HRID 2237769Notes

Reaction equation

HRID 2237769 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1.[CH2:12]([O:14][C:15]1[C:24]2[C:19](=[CH:20][C:21]([F:25])=[CH:22][CH:23]=2)[C:18]([O:26][CH2:27][CH3:28])=[C:17]([C:29](O)=[O:30])[C:16]=1[C:32](O)=[O:33])[CH3:13]>CN1C(=O)CCC1.CCOC(C)=O>[CH2:27]([O:26][C:18]1[C:17]2[C:29](=[O:30])[N:1]([C:2]3[CH:3]=[CH:4][C:5]([CH2:8][C:9]([OH:11])=[O:10])=[CH:6][CH:7]=3)[C:32](=[O:33])[C:16]=2[C:15]([O:14][CH2:12][CH3:13])=[C:24]2[CH:23]=[CH:22][C:21]([F:25])=[CH:20][C:19]=12)[CH3:28]

Participants

5

Reactant 2

HCID 145334-Aminophenylacetic acidHCID 57557633HCID 57557633, compound

Product 1

HCID 17747304HCID 17747304, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
180 °C

Procedure

4-Aminophenylacetic acid (418 mg, 2.77 mmol) was added to 1,4-bis(ethyloxy)-6-fluoro-2,3-naphthalenedicarboxylic acid (810 mg, 2.5 mmol) and powdered molecular sieves (4 Å, 200 mg) in NMP (4.5 ml) and heated in a microwave at 180° C. for 10 minutes. The reaction mixture was cooled and diluted with EtOAc, filtered through celite, washed with water, brine, dried over magnesium sulphate and concentrated in vacuo to yield a yellow solid. This was recrystallised from methanol (˜50 ml) and the white solid filtered, washed with methanol and dried in vacuo in an oven to give the title compound as a white solid (490 mg, 1.1 mmol). The filtrate was concentrated in vacuo and the yellow oil purified by reverse phase chromatography eluting with acetonitrile:water (1:20-1:0) to give the title compound as a white solid (107 mg, 0.24 mmol).

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationfiltered through celite
  3. washwashed with water, brine
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated in vacuo
  6. customto yield a yellow solid
  7. customThis was recrystallised from methanol (˜50 ml)
  8. filtrationthe white solid filtered
  9. washwashed with methanol
  10. customdried in vacuo in an oven

Sources & evidence

ORD record
ord-79575d4dd37242418880ce0dfc9d3b19
Source dataset
uspto-grants-2010_05
Patent number
US07718689B2

Reaction notes

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