Pyridine → HCID 53985361, compound

HRID 2398925Notes

Reaction equation

HRID 2398925 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8](Cl)=[O:9])=[CH:6][CH:5]=1)([O-])=O.[CH2:13]([O:17][P:18]([CH:25]([OH:28])[CH2:26][CH3:27])(=[O:24])[O:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH2:14][CH2:15][CH3:16].N1C=CC=CC=1.[H][H]>C(#N)C>[CH2:13]([O:17][P:18]([CH:25]([O:28][C:8](=[O:9])[C:7]1[CH:11]=[CH:12][C:4]([NH2:1])=[CH:5][CH:6]=1)[CH2:26][CH3:27])(=[O:24])[O:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH2:14][CH2:15][CH3:16]

Participants

6

Reactant 4

HCID 1049PyridineHCID 85024-Nitrobenzoyl chlorideHCID 54519346HCID 54519346, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 53985361HCID 53985361, compoundYield 42.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of 15 g of 4-nitro-benzoyl chloride in 100 ml of acetonitrile is added dropwise to a solution of 20 g of α-hydroxy-propanephosphonic acid dibutyl ester and 8 g of pyridine in 20 ml of acetonitrile at 0° C. After 16 hours the mixture is filtered, the filtrate is evaporated and the residue is extracted with 200 ml of diethyl ether. After evaporation, and purification by column chromatography, 13 g of pure α-(4-nitro-benzoyloxy)-propanephosphonic acid dibutyl ester are obtained. This is reduced with hydrogen as indicated in Example 2. 12.5 g of α-(4-amino-benzoyl-oxy)-propanephosphonic acid dibutyl ester are obtained. After condensation with o-methoxybenzoylacetic acid methyl ester according to Example 6, and purification by column chromatography, the compound of the formula (142 ) is obtained in the form of a yellow resin.

Workup

  1. filtrationAfter 16 hours the mixture is filtered
  2. customthe filtrate is evaporated
  3. extractionthe residue is extracted with 200 ml of diethyl ether
  4. customAfter evaporation, and purification by column chromatography, 13 g of pure α-(4-nitro-benzoyloxy)-propanephosphonic acid dibutyl ester
  5. customare obtained

Sources & evidence

ORD record
ord-8812e48a5fc5468c9976c53db19f5da8
Source dataset
uspto-grants-1977_05
Patent number
US04026709

Reaction notes

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