Sodium Carbonate → Diethyl (4-aminophenyl)phosphonate

HRID 1241347Notes

Reaction equation

HRID 1241347 reaction equation
[CH2:1]([O:3][P:4]([C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][CH:10]=1)(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2].Cl[Sn]Cl.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[CH2:6]([O:5][P:4]([C:9]1[CH:10]=[CH:11][C:12]([NH2:15])=[CH:13][CH:14]=1)(=[O:8])[O:3][CH2:1][CH3:2])[CH3:7]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 24479Stannous ChlorideHCID 284865Diethyl(4-nitrophenyl)phosphonate

Product 1

HCID 273213Diethyl (4-aminophenyl)phosphonateYield 88.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(4-Nitro-phenyl)-phosphonic acid diethyl ester (7.6 g, 29.1 mmol) and SnCl2 (29.6 g, 0.13 mmol) were heated at reflux for 1 h. The mixture was poured in CH2Cl2 (500 mL) and adjusted to pH 8 with sat'd Na2CO3. The resulting mixture was filtered through Celite (CH2Cl2 wash) and the layers separated. The aqueous layer was extracted with CH2Cl2 and the combined extracts, were washed with water, sat'd NaCl, then dried over MgSO4 and filtered. Concentration yielded a light yellow solid (5.9 g, 88%): MS [M+H]+ 230; m.p. 117–118° C.

Workup

  1. temperatureat reflux for 1 h
  2. filtrationThe resulting mixture was filtered through Celite (CH2Cl2 wash)
  3. customthe layers separated
  4. extractionThe aqueous layer was extracted with CH2Cl2
  5. washthe combined extracts, were washed with water
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationConcentration

Sources & evidence

ORD record
ord-168167e04f0240d7b101b24939508a2a
Source dataset
uspto-grants-2006_10
Patent number
US07115589B2

Reaction notes

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