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Sodium Hydroxide → HCID 21873753, 화합물

HRID 639016
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HRID 639016 반응식
Br[C:2]1[CH:3]=[C:4]2[O:16][CH2:15][CH2:14][O:13][C:5]2=[C:6]2[C:11]=1[NH:10][CH:9]=[CH:8][C:7]2=[O:12].[OH-].[Na+]>O.O1CCOCC1.[Pd]>[O:13]1[C:5]2=[C:6]3[C:11](=[CH:2][CH:3]=[C:4]2[O:16][CH2:15][CH2:14]1)[NH:10][CH:9]=[CH:8][C:7]3=[O:12]
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참가 물질

5

반응물 2

HCID 14798Sodium HydroxideHCID 21873662HCID 21873662, 화합물

생성물 1

HCID 21873753HCID 21873753, 화합물수율 114.8%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 218864351,4-Dioxane--water (1/1)용매

실험 절차

A suspension of 6-bromo-2,3-dihydro-7H-[1,4]dioxino[2,3-f]quinolin-10-one (3.4 g, 12 mmol) in water/dioxane (150 mL/80 mL) was treated with 1M aqueous sodium hydroxide solution then hydrogenated over 10% palladium on charcoal (1.5 g) for 20 hours. The mixture was filtered then acidified with 5M aqueous hydrochloric acid. On concentrating to ca 100 mL, a solid began to crystallise out. The mixture was stored at 5° C. overnight. Filtration and drying afforded a pale yellow solid (2.8 g, 100%). LC/MS (ES) m/z 203 (MH+ 92%); 1H-NMR (400 MHz, d6-DMSO), 11.4 (1H, s, NH), 7.64 (1H, d, J=7.2, CHNHC), 7.15 (1H, d, J=9.2, CHCO), 6.95 (1H, d, J=8.8, CHCN), 5.80 (1H, d, J=7.2, CH═CO), 4.26-4.27 (4H, m, 2×(CH2O)).

후처리

  1. filtrationThe mixture was filtered
  2. concentrationOn concentrating to ca 100 mL
  3. customto crystallise out
  4. filtrationFiltration
  5. customdrying

출처 및 근거

ORD 기록
ord-8a31f9cbe0334ab5b718bafd3db4919e
출처 데이터셋
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07691850B2

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