Sodium Carbonate → (4-Amino-2-chloro-5-methoxy-benzyl)-phosphonic acid diethylester

HRID 2279872Notes

Reaction equation

HRID 2279872 reaction equation
[CH2:1]([O:3][P:4]([CH2:9][C:10]1[CH:15]=[C:14]([O:16][CH3:17])[C:13]([N+:18]([O-])=O)=[CH:12][C:11]=1[Cl:21])(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2].C([O-])([O-])=O.[Na+].[Na+]>Cl.C(O)C.C(OCC)(=O)C.[Fe]>[CH2:1]([O:3][P:4]([CH2:9][C:10]1[CH:15]=[C:14]([O:16][CH3:17])[C:13]([NH2:18])=[CH:12][C:11]=1[Cl:21])(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2]

Participants

7

Reactant 2

HCID 10340Sodium CarbonateHCID 86697809(2-Chloro-5-methoxy-4 nitrobenzyl)-phosphonic acid diethylester2×

Product 1

HCID 86697808(4-Amino-2-chloro-5-methoxy-benzyl)-phosphonic acid diethylesterYield 85.2%

Reagents, catalysts & solvents 4

HCID 23925IronCatalystHCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of (2-chloro-5-methoxy-4 nitrobenzyl)-phosphonic acid diethylester (Compound 56F, 10.3 g, 30.5 mmol), iron powder (16.8 g, 305 mmol) in 2M aqueous hydrochloric acid (25 mL) and ethanol (150 mL) was heated to reflux for 1 hr. The reaction mixture was cooled to RT and solid Na2CO3 (6 g) was added until the pH was 9. The reaction mixture was filtered through celite, the filter cake was washed with dichloromethane and the filtrate was concentrated to give a residue which was dissolved in ethyl acetate, washed with water, dried over sodium sulfate, filtered and concentrated to give the required material as gum (8 g, 85%). 1H NMR (400 MHz, CDCl3) δ: 6.88 (s, 1H), 6.71 (s, 1H), 4.3 (brs, 2H), 4.05-4.13 (m, 4H), 3.85 (s, 3H), 3.26 (d, J=20.50 Hz, 2H), 1.28 (t, J=7.05 Hz, 6H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 1 hr
  3. filtrationThe reaction mixture was filtered through celite
  4. washthe filter cake was washed with dichloromethane
  5. concentrationthe filtrate was concentrated
  6. customto give a residue which
  7. washwashed with water
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-8092cb5c0f8e419b87e69570a1743e4c
Source dataset
uspto-grants-2015_09
Patent number
US09133224B2

Reaction notes

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