Stannous chloride dihydrate → 4-(2-Chloroethoxy)aniline

HRID 735812

반응식

HRID 735812 반응식
ClCC[O:4]C1C=CC([NH2:11])=CC=1.[Cl:12][CH2:13][CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][CH:17]=1.O.O.Cl[Sn]Cl>C(O)C>[NH4+:11].[OH-:4].[Cl:12][CH2:13][CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][CH:17]=1

참가 물질

6

반응물 3

HCID 61436Stannous chloride dihydrateHCID 1196994-(2-Chloroethoxy)anilineHCID 27645871-(2-Chloroethoxy)-4-nitrobenzene

생성물 2

HCID 14923Ammonium HydroxideHCID 1196994-(2-Chloroethoxy)aniline수율 90%

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
70 °C

실험 절차

4-(2-Chloro-ethoxy)-phenylamine can be synthesized by the following procedure. A suspension of 1-(2-chloro-ethoxy)-4-nitro-benzene (1.5 mmol) (from Example 1c) and SnCl2.2H2O (5.9 mmol) in absolute ethanol (120 mL) is heated at 70° C. for 2 h. The solvent is removed under vacuum and the residue is dissolved in 5% NaOH and extracted with EtOAc (3×50 mL). The organic layer is washed with 5% NaOH (1×50 mL), water (1×50 mL), brine, and dried over Na2SO4 and reduced to dryness. The dark crude residue is purified by silica chromatography using a mixture of DCM:MeOH:NH4OH=9:1:0.1 to isolate 4-(2-chloro-ethoxy)-phenylamine (90%) which is converted in the hydrochloride salt by treatment with HCl (1 eq of a 4N solution in dioxane). 1HNMR (400 MHz, CD3OD) δ 7.35-7.33 (m, 2H), 7.16-7.05 (m, 2H), 4.38 (m, 2H), 3.87 (m, 2H). MS (m/z) (M+1)+173.1.

후처리

  1. customThe solvent is removed under vacuum
  2. dissolutionthe residue is dissolved in 5% NaOH
  3. extractionextracted with EtOAc (3×50 mL)
  4. washThe organic layer is washed with 5% NaOH (1×50 mL), water (1×50 mL), brine
  5. dry with materialdried over Na2SO4
  6. customThe dark crude residue is purified by silica chromatography
  7. additiona mixture of DCM

출처 및 근거

ORD 기록
ord-5b93a1b87b51441cbb886d616b2071c7
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07592349B2

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