4-Aminobenzoic Acid → HCID 18510721, compound

HRID 2219086Notes

Reaction equation

HRID 2219086 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.C(N(C(C)C)C(C)C)C.Cl.[N:21]1[CH:26]=[CH:25][CH:24]=[C:23]([C:27]2[CH2:31][CH:30]([C:32](Cl)=[O:33])[O:29][N:28]=2)[CH:22]=1>C(Cl)Cl>[N:21]1[CH:26]=[CH:25][CH:24]=[C:23]([C:27]2[CH2:31][CH:30]([C:32]([NH:1][C:2]3[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=3)=[O:33])[O:29][N:28]=2)[CH:22]=1

Participants

5

Reactant 3

HCID 9784-Aminobenzoic AcidHCID 81531DiisopropylethylamineHCID 18510746HCID 18510746, compound

Product 1

HCID 18510721HCID 18510721, compoundYield 36.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-aminobenzoic acid (0.020 mol) and N-ethyl-N-(1-methylethyl)-2-propanamine, (0.020 mol) in CH2Cl2 (100 ml) was cooled to 0° C. (±)-4,5-dihydro-3-(3-pyridinyl)-5-isoxazolecarbonyl chloride monohydrochloride (0.020 mol) was added. The resulting brown suspension was stirred overnight. The precipitate was filtered off, washed with CH2Cl2, then dried. The filtrate was evaporated under reduced pressure. The residue was purified by short column chromatography over silica gel (eluent: CH2Cl2/CH3OH 95/5). The pure fractions were collected and the solvent was evaporated under reduced pressure. The residue was stirred in methanol, filtered off, then dried, yielding 2.3 g of (±)-4-[[[4,5-dihydro-3-(3-pyridinyl)-5-isoxazolyl]-carbonyl]amino]benzoic acid (interm. 19).

Workup

  1. additionwas added
  2. filtrationThe precipitate was filtered off
  3. washwashed with CH2Cl2
  4. customdried
  5. customThe filtrate was evaporated under reduced pressure
  6. customThe residue was purified by short column chromatography over silica gel (eluent: CH2Cl2/CH3OH 95/5)
  7. customThe pure fractions were collected
  8. customthe solvent was evaporated under reduced pressure
  9. stirringThe residue was stirred in methanol
  10. filtrationfiltered off
  11. customdried

Sources & evidence

ORD record
ord-dffc631e7abc4431a665fe7454193103
Source dataset
uspto-grants-2008_08
Patent number
US07414048B2

Reaction notes

Loading…