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p-Toluenesulfonic acid monohydrate → Toluene-4-sulfonic acid 5-amino-3,4-dihydro-2H-benzo[1,4]oxazin-3-ylmethyl ester

HRID 896010
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HRID 896010 반응식
[N+:1]([C:4]1[C:9]2[NH:10][CH:11]([CH2:14][O:15][S:16]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)(=[O:18])=[O:17])[CH2:12][O:13][C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-])=O.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[H][H]>[Pd].CO>[NH2:1][C:4]1[C:9]2[NH:10][CH:11]([CH2:14][O:15][S:16]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)(=[O:18])=[O:17])[CH2:12][O:13][C:8]=2[CH:7]=[CH:6][CH:5]=1
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참가 물질

6

반응물 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 20814149Toluene-4-sulfonic acid 5-nitro-3,4-dihydro-2H-benzo[1,4]oxazin-3-ylmethyl esterHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 20814150Toluene-4-sulfonic acid 5-amino-3,4-dihydro-2H-benzo[1,4]oxazin-3-ylmethyl ester수율 200.4%

시약·촉매·용매 2

HCID 23938Palladium
촉매
HCID 887Methanol용매

실험 절차

A mixture of toluene-4-sulfonic acid 5-nitro-3,4-dihydro-2H-benzo[1,4]oxazin-3-ylmethyl ester (3.64 g, 10.0 mmole), p-toluenesulfonic acid monohydrate (3.8 g, 20.0 mmole) and 0.50 g of 10% palladium on carbon in 140 mL of methanol was treated with 50 psi of hydrogen on a Parr shaker for 1 hour. The catalyst was filtered and washed with additional methanol. The solvent was evaporated in vacuum to yield 6.7 g of the p-toluenesulfonate salt of the title compound as a pink solid. This compound was used for the next step without further purification.

후처리

  1. filtrationThe catalyst was filtered
  2. washwashed with additional methanol
  3. customThe solvent was evaporated in vacuum

출처 및 근거

ORD 기록
ord-f88f303f24024466a7bbdea2114794a6
출처 데이터셋
uspto-grants-2005_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06919334B2

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