Hydrochloric Acid → HCID 67052723, compound

HRID 921319Notes

Reaction equation

HRID 921319 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][P:11](=[O:25])([C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[C:16]([O:23][CH3:24])[CH:15]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)C.Cl>[Fe].O>[CH2:1]([N:8]1[CH2:9][CH2:10][P:11]([C:14]2[CH:19]=[CH:18][C:17]([NH2:20])=[C:16]([O:23][CH3:24])[CH:15]=2)(=[O:25])[CH2:12][CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 68158036HCID 68158036, compound

Product 1

HCID 67052723HCID 67052723, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Conditions

Temperature
95 °C

Procedure

To a solution of 1-benzyl-4-(3-methoxy-4-nitrophenyl)-1,4-azaphosphinane 4-oxide (0.224 g, 0.622 mmol) in 0.6 mL 4:1 ethanol:water was added iron powder (0.348 g, 6.22 mmol) and 0.30 mL ethanolic HCl (2.5 M). The reaction vessel was sealed and was heated to 95° C. for 1 h. The reaction mixture was cooled to rt, filtered, and concentrated. The crude residue was purified by silica gel chromatography (0-5% 7N ammonia in methanol:dichloromethane) to afford the desired product (86.1 mg, 42% yield).

Workup

  1. customThe reaction vessel was sealed
  2. temperatureThe reaction mixture was cooled to rt
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude residue was purified by silica gel chromatography (0-5% 7N ammonia in methanol:dichloromethane)

Sources & evidence

ORD record
ord-69eb6877739346e592c07f3520ca749c
Source dataset
uspto-grants-2016_03
Patent number
US09273077B2

Reaction notes

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