Hydrochloric Acid → HCID 178510679、化合物

HRID 255000ノート

反応式

HRID 255000 の反応式
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

参加物

11

反応物 7

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

生成物 1

HCID 178510679HCID 178510679、化合物収率 68.6%

試薬・触媒・溶媒 3

HCID 702Ethanol溶媒HCID 962Water溶媒HCID 21962138N,N-Dimethylformamide--water (1/1)溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-782c6a7f13db494b810a81dddfdb6932
出典データセット
uspto-grants-2011_01
特許番号
US07875728B2

反応ノート

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