Hydroxyamine hydrochloride → HCID 86745180, 화합물

HRID 345772

반응식

HRID 345772 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=O.C(C1C=NC=CC=1NC(=O)C(C)(C)C)=O.C1([Mg][Cl:38])C=CC=CC=1.Cl.[NH2:40][OH:41]>N1C=CC=CC=1>[ClH:38].[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[N:40][OH:41]

참가 물질

6

반응물 4

HCID 443297Hydroxyamine hydrochlorideHCID 2779664N-(3-formylpyridin-4-yl)-2,2-dimethylpropanamideHCID 13701094HCID 13701094, 화합물HCID 178478979HCID 178478979, 화합물

생성물 1

HCID 86745180HCID 86745180, 화합물

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

A solution of (4-amino-3-pyridinyl)phenylmethanone (17 g prepared from N-(3-formyl-4-pyridinyl)-2,2-dimethylpropanamide by utilizing the reaction scheme described in Example 9, 10 and 11 except that phenyl magnesium chloride was used instead of cyclohexyl magnesium chloride) and hydroxylamine hydrochloride (24 g) in 150 ml pyridine was stirred at 90°-95° for two hours and thereafter cooled and concentrated. The residue was stirred with water, basified with sodium carbonate and extracted with dichloromethane. The dried organic layer was concentrated to 20 g waxy solid. This was triturated with acetonitrile to yield 13.6 g solid, m.p. 177°-179°. The filtrate was concentrated to 4.3 g oil and thereafter eluted with 10% methanol in dichloromethane through silica via flash column chromatography to yield an additional 1.8 g product for a total yield of 15.4 g. Eight grams were again eluted with 10% methanol in dichloromethane through silica via flash column chromatography to yield 6.9 g solid, m.p. 178°-180°. A 4.9 g portion was converted to the hydrochloride salt in methanol/ether to yield 3.3 g crystals, d 238°-240°.

후처리

  1. customthe reaction scheme
  2. temperaturecooled
  3. concentrationconcentrated
  4. stirringThe residue was stirred with water
  5. extractionextracted with dichloromethane
  6. concentrationThe dried organic layer was concentrated to 20 g waxy solid
  7. customThis was triturated with acetonitrile

출처 및 근거

ORD 기록
ord-68d2d485768641729c23fe53ae860240
출처 데이터셋
uspto-grants-1991_10
특허 번호
US05059602

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