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Triethylamine → 8-Amino-1-methyl-1,3,4,5-tetrahydro-benzo[B]azepin-2-one

HRID 1040644
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HRID 1040644 반응식
CC1[N:3]([C:8]2[CH:9]=[CH:10][C:11]3[CH2:17][CH2:16][CH2:15][C:14](=[O:18])[N:13]([CH3:19])[C:12]=3[CH:20]=2)C(C)=CC=1.Cl.NO.C(N(CC)CC)C>C(O)C.O>[NH2:3][C:8]1[CH:9]=[CH:10][C:11]2[CH2:17][CH2:16][CH2:15][C:14](=[O:18])[N:13]([CH3:19])[C:12]=2[CH:20]=1
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참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochlorideHCID 672642018-(2,5-Dimethyl-pyrrol-1-yl)-1-methyl-1,3,4,5-tetrahydro-benzo[b]azepin-2-one

생성물 1

HCID 197601958-Amino-1-methyl-1,3,4,5-tetrahydro-benzo[B]azepin-2-one수율 889.6%

시약·촉매·용매 1

HCID 19096565Water ethanol용매

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온도
80 °C

실험 절차

8-(2,5-Dimethyl-pyrrol-1-yl)-1-methyl-1,3,4,5-tetrahydro-benzo[b]azepin-2-one (175 mgs, 0.065 mmol) was treated with hydroxylamine hydrochloride (20 eq), triethylamine (10 eq) in ethanol/water (4:1, 6 mL) and heated to 80° C. overnight. The mixture was concentrated, partitioned between EtOAc and water, dried (MgSO4) filtered and concentrated. The mixture was stirred 2 h with excess 1N HCl, neutralized to pH 7 with 1 NaOH, partitioned between EtOAc and water, dried (MgSO4) filtered and concentrated to give 8-Amino-1-methyl-1,3,4,5-tetrahydro-benzo[b]azepin-2-one (110 mgs, 58%). 6.95 (d, J=7.8 Hz, 1H), 6.50-6.47 (m, 2H), 3.67 (br s, 2H), 3.30 (s, 3H), 2.61-2.57 (m, 2H), 2.32-2.28 (m, 2H), 2.11-2.08 (m, 2H).

후처리

  1. concentrationThe mixture was concentrated
  2. custompartitioned between EtOAc and water
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompartitioned between EtOAc and water
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated

출처 및 근거

ORD 기록
ord-fdec67340b5b429b9af022cf860188fc
출처 데이터셋
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08552186B2

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