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Sodium Bicarbonate → 3-[3-[(2Z)-2-[1-(2,3-dihydro-1H-inden-5-yl)-3-methyl-5-(oxomethylidene)pyrazol-4-ylidene]hydrazinyl]-2-hydroxyphenyl]benzoic acid

HRID 238699
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HRID 238699 반응식
Br.[NH2:2][C:3]1[C:4]([OH:18])=[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([OH:17])=[O:16])[CH:10]=2)[CH:6]=[CH:7][CH:8]=1.[N:19]([O-])=O.[Na+].[CH2:23]1[C:31]2[C:26](=[CH:27][C:28]([N:32]3[C:36](=[O:37])[CH2:35][C:34]([CH3:38])=[N:33]3)=[CH:29][CH:30]=2)[CH2:25][CH2:24]1.[C:39](=[O:42])(O)[O-].[Na+]>Cl.C(O)C>[OH:18][C:4]1[C:3]([NH:2]/[N:19]=[C:35]2/[C:34]([CH3:38])=[N:33][N:32]([C:28]3[CH:27]=[C:26]4[C:31](=[CH:30][CH:29]=3)[CH2:23][CH2:24][CH2:25]4)[C:36]/2=[O:37])=[CH:8][CH:7]=[CH:6][C:5]=1[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([OH:17])=[O:16])[CH:10]=1.[OH:18][C:4]1[C:3]([NH:2]/[N:19]=[C:35]2\[C:34]([CH3:38])=[N:33][N:32]([C:28]3[CH:27]=[C:26]4[C:31](=[CH:30][CH:29]=3)[CH2:23][CH2:24][CH2:25]4)[C:36]\2=[C:39]=[O:42])=[CH:8][CH:7]=[CH:6][C:5]=1[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([OH:17])=[O:16])[CH:10]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 516892Sodium BicarbonateHCID 23668193Sodium NitriteHCID 574837802-Indan-5-yl-5-methyl-2,4-dihydro-pyrazol-3-oneHCID 574837893'-Amino-2'-hydroxy-biphenyl-3-carboxylic acid hydrobromide

생성물 2

HCID 1765211573-[3-[(2Z)-2-[1-(2,3-dihydro-1H-inden-5-yl)-3-methyl-5-(oxomethylidene)pyrazol-4-ylidene]hydrazinyl]-2-hydroxyphenyl]benzoic acid수율 11.4%
HCID 178433789HCID 178433789, 화합물

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 702Ethanol용매

실험 절차

Upon cooling by an ice-water bath, 3′-amino-2′-hydroxy-biphenyl-3-carboxylic acid hydrobromide 1f (267 mg, 1.16 mmol) was dissolved in 10 mL of 1M hydrochloric acid followed by dropwise addition of 10 mL of sodium nitrite solution (88 mg, 1.28 mmol) and 2-indan-5-yl-5-methyl-2,4-dihydro-pyrazol-3-one 1i (249 mg, 1.16 mmol). The mixture was adjusted to pH 8 with saturated sodium bicarbonate solution, followed by addition of 10 mL of ethanol. The reaction mixture was warmed up to room temperature overnight. The mixture was filtered, dried and recrystallized from methanol to obtain the title compound (Z)-2′-hydroxy-3′-[N′-(1-indan-5-yl-3-methyl-5-carbonyl-1,5-dihydro-pyrazol-4-ylidene)-hydrazino]-biphenyl-3-carboxylic acid 1j (60 mg, yield 11.4%) as a yellow solid.

후처리

  1. temperatureUpon cooling by an ice-water bath
  2. filtrationThe mixture was filtered
  3. customdried
  4. customrecrystallized from methanol

출처 및 근거

ORD 기록
ord-2d68a287958c4ec4b2a7a96acc35eda3
출처 데이터셋
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08642637B2

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