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

HRID 2279872
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HRID 2279872 반응식
[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]
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참가 물질

7

반응물 2

HCID 10340Sodium CarbonateHCID 86697809(2-Chloro-5-methoxy-4 nitrobenzyl)-phosphonic acid diethylester2회

생성물 1

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

시약·촉매·용매 4

HCID 23925Iron촉매HCID 313Hydrochloric Acid용매
HCID 702
Ethanol
용매
HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-8092cb5c0f8e419b87e69570a1743e4c
출처 데이터셋
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09133224B2

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