Pyridine → HCID 23374549, compound

HRID 1756452Notes

Reaction equation

HRID 1756452 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]([NH2:12])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].N1C=CC=CC=1.[CH3:19][C:20]1([CH3:37])[CH2:29][CH2:28][C:27]([CH3:31])([CH3:30])[C:26]2[CH:25]=[C:24]([C:32](=[O:36])[C:33](Cl)=[O:34])[CH:23]=[CH:22][C:21]1=2.C12(C3C=C(NC(=O)NC4C=CC(C(OC)=O)=CC=4)C=CC=3OC)CC3CC(CC(C3)C1)C2>C1COCC1.O>[OH:1][C:2]1[CH:11]=[C:10]([NH:12][C:33]([C:32]([C:24]2[CH:23]=[CH:22][C:21]3[C:20]([CH3:37])([CH3:19])[CH2:29][CH2:28][C:27]([CH3:31])([CH3:30])[C:26]=3[CH:25]=2)=[O:36])=[O:34])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

7

Reactant 4

HCID 1049PyridineHCID 77787Methyl p-aminosalicylateHCID 21267541HCID 21267541, compoundHCID 67714159Methyl 4-[3-(1-adamantyl)-4-methoxyphenylureido]benzoate

Product 1

HCID 23374549HCID 23374549, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

6.7 g (40 mmol) of methyl 2-hydroxy-4-aminobenzoate, 10 ml (0.12 mol) of pyridine and 50 ml of THF are introduced into a round-bottomed flask. A solution of 10.5 g (40 mmol) of 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl -2-naphthylglyoxyloyl chloride, prepared in 1 (c), in 100 ml of THF is added dropwise and the mixture is stirred at room temperature for 4 h. The reaction medium is poured into water, the mixture is extracted with ethyl ether and the organic phase is separated after settling has taken place, dried over magnesium sulphate and evaporated. The residue obtained is purified by chromatography on a silica column and eluted with a mixture of dichloromethane and hexane (30:70). After evaporation of the solvents, 7.3 g (45%) of methyl ester, melting point 146°-147° C., are collected.

Workup

  1. additionis added dropwise
  2. extractionthe mixture is extracted with ethyl ether
  3. customthe organic phase is separated after settling
  4. dry with materialdried over magnesium sulphate
  5. customevaporated
  6. customThe residue obtained
  7. customis purified by chromatography on a silica column
  8. washeluted with a mixture of dichloromethane and hexane (30:70)
  9. customAfter evaporation of the solvents, 7.3 g (45%) of methyl ester, melting point 146°-147° C.
  10. customare collected

Sources & evidence

ORD record
ord-7852f60c4a4841f0864e255c514ab552
Source dataset
uspto-grants-1995_08
Patent number
US05439925

Reaction notes

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