Hydrochloric Acid → HCID 178510679, compound

HRID 255000Notes

Reaction equation

HRID 255000 reaction equation
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

Participants

11

Reactant 7

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

Product 1

HCID 178510679HCID 178510679, compoundYield 68.6%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 21962138N,N-Dimethylformamide--water (1/1)Solvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-782c6a7f13db494b810a81dddfdb6932
Source dataset
uspto-grants-2011_01
Patent number
US07875728B2

Reaction notes

Loading…