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Acetic Acid → 6-(aminomethyl)-2,2-dimethyl-4H-1,3-benzodioxin-4-one acetate

HRID 902768
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HRID 902768 반응식
[CH3:1][C:2]1([CH3:15])[O:7][C:6]2[CH:8]=[CH:9][C:10]([C:12]#[N:13])=[CH:11][C:5]=2[C:4](=[O:14])[O:3]1.C(O)(=O)C.N#N>CO.[Pd]>[C:2]([OH:7])(=[O:3])[CH3:1].[NH2:13][CH2:12][C:10]1[CH:9]=[CH:8][C:6]2[O:7][C:2]([CH3:15])([CH3:1])[O:3][C:4](=[O:14])[C:5]=2[CH:11]=1
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참가 물질

6

반응물 3

HCID 176Acetic AcidHCID 947NitrogenHCID 597024522,2-dimethyl-4-oxo-4H-1,3-benzodioxine-6-carbonitrile

생성물 1

HCID 674204786-(aminomethyl)-2,2-dimethyl-4H-1,3-benzodioxin-4-one acetate수율 74.8%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol
용매

실험 절차

To a solution of 2,2-dimethyl-4-oxo-4H-1,3-benzodioxine-6-carbonitrile (12 g, 0.06 mol) in methanol (500 mL) was added glacial acetic acid (3.5 g, 0.059 mol) and passed N2 for 30 min. To this was added Pd/C (2.4 g, 20%) and hydrogenated under 2 Bars of pressure for 22 h. The reaction mixture was filtered through celite and filtrate concentrated under vacuum. To the solid was added EtOAc (200 mL), stirred for 20 h and filtered. The solid was dried under vacuum to give the title compound (6 g, 38%). TLC: CHCl3/MeOH, 9:1, Rf: 0.15

후처리

  1. customfor 30 min
  2. filtrationThe reaction mixture was filtered through celite and filtrate
  3. concentrationconcentrated under vacuum
  4. additionTo the solid was added EtOAc (200 mL)
  5. filtrationfiltered
  6. customThe solid was dried under vacuum

출처 및 근거

ORD 기록
ord-92ab9ae019f1428681d09fc226c72fd6
출처 데이터셋
uspto-grants-2008_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07365225B2

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