Hydrochloric Acid → HCID 178510679, 화합물

HRID 2095166노트

반응식

HRID 2095166 반응식
FC1C=C(C=CC=1)N.Cl.N([O-])=O.[Na+].O=C1C2C(=CC=CC=2)C(=O)N1CC(=O)CC#N.CC([O-])=O.[Na+].[NH2:36][C:37]1[C:38](=[N:54][NH:55][C:56]2[CH:61]=[CH:60][CH:59]=[C:58]([F:62])[CH:57]=2)[C:39]([CH2:42][N:43]2C(=O)C3C(=CC=CC=3)C2=O)=[N:40][N:41]=1.NN>O.CN(C=O)C.O.C(O)C>[NH2:43][CH2:42][C:39]1[C:38](=[N:54][NH:55][C:56]2[CH:61]=[CH:60][CH:59]=[C:58]([F:62])[CH:57]=2)[C:37]([NH2:36])=[N:41][N:40]=1

참가 물질

11

반응물 7

HCID 313Hydrochloric AcidHCID 9321HydrazineHCID 97423-FluoroanilineHCID 517045Sodium AcetateHCID 23668193Sodium NitriteHCID 668449574-(1,3-Dioxo-1,3-dihydroisoindol-2-yl)-3-oxobutyronitrileHCID 178509152HCID 178509152, 화합물

생성물 1

HCID 178510679HCID 178510679, 화합물수율 68.6%

시약·촉매·용매 3

HCID 702Ethanol용매HCID 962Water용매HCID 21962138N,N-Dimethylformamide--water (1/1)용매

실험 절차

A solution of 3-fluoroaniline (1.67 g, 15 mmole) in 17 mL of water, acidified with 3.75 mL of conc. HCl (45 mmole) in an ice bath, was treated with NaNO2 (1.35 g, 19.5 mmole). The diazonium solution was then added to the solution of 4-(1,3-dioxo-1,3-dihydroisoindol-2-yl)-3-oxobutyronitrile (2.28 g, 10 mmole) with NaOAc (6.12 g, 45 mmole) in DMF/water mixture (30:35 mL). From this reaction, 3.4 g of 2-{5-amino-4-[(3-fluorophenyl)hydrazono]-4H-pyrazol-3-ylmethyl}isoindole-1,3-dione, as a yellow powder, was obtained, which was then treated with hydrazine (22 mmole) portionwise in hot ethanol. After the reaction was completed, a few grams of silica gel was mixed and the solvent was evaporated. The powdery residue was purified by column chromatography (CH2Cl2:MeOH:NH3.H2O=600:150:6) to yield 1.5 g (61%) of the title compound as an orange powder. 1H NMR (ppm, 200 MHz, DMSO-d6) δ 7.40-7.70 (m, 3H), 7.12 (m, 1H), 7.00 (br s, 2H), 4.01 (s, 2H).

후처리

  1. customas a yellow powder, was obtained
  2. additiona few grams of silica gel was mixed
  3. customthe solvent was evaporated
  4. customThe powdery residue was purified by column chromatography (CH2Cl2:MeOH:NH3.H2O=600:150:6)

출처 및 근거

ORD 기록
ord-aaebe0a6303a4499a00ef5d7b8c0a671
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08445694B2

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