Hydrochloric Acid → HCID 178489125, compound

HRID 271100Notes

Reaction equation

HRID 271100 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:10][C:9]([NH2:18])=[CH:8][CH:7]=1.[N:19]([O-])=O.[Na+].Cl.[CH3:24][O:25][C:26]1[CH:27]=[C:28]([C:34]2[CH2:35][C:36](=[O:39])[NH:37][N:38]=2)[CH:29]=[CH:30][C:31]=1[O:32][CH3:33].C([O-])(=O)C.[Na+]>O.C(O)C>[Br:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:10][C:9]([NH:18][N:19]=[C:35]2[C:34]([C:28]3[CH:29]=[CH:30][C:31]([O:32][CH3:33])=[C:26]([O:25][CH3:24])[CH:27]=3)=[N:38][NH:37][C:36]2=[O:39])=[CH:8][CH:7]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 517045Sodium AcetateHCID 152835193-(3,4-dimethoxyphenyl)-4,5-dihydro-1H-pyrazol-5-oneHCID 223532056-(3-Bromo-propoxy)-biphenyl-3-ylamineHCID 23668193Sodium Nitrite

Product 1

HCID 178489125HCID 178489125, compoundYield 27.2%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent2×

Procedure

6-(3-Bromo-propoxy)-biphenyl-3-ylamine (r, 250 mg, 0.82 mmol) was diazotized with sodium nitrite (67 mg, 0.98 mmol) in 1:1 water/ethanol and 0.5 mL concentrated HCl at 0° C. After approximately 1 hour, the diazonium solution was added dropwise to a suspension of 5-(3,4-dimethoxy-phenyl)-2,4-dihydro-pyrazol-3-one (200 mg, 0.9 mmol) and sodium acetate (1.1 g) in 10 mL 1:1 water/ethanol. The orange solid which precipitated was filtered and washed with water and dried. The crude product was purified by silica gel chromatography (eluent: 5% methanol/DCM) to afford 120 mg of 4-{[6-(3-bromo-propoxy)-biphenyl-3-yl]-hydrazono}-5-(3,4-dimethoxy-phenyl)-2,4-dihydro-pyrazol-3-one (s): HPLC (Rt) 5.02 min; m/e 536.1, MS (ES+): 538.9; 1H NMR (500 MHz, CDCl3): 13.9 (bs, 1H), 9.0 (bs, 1H), 7.7-6.9 (m, 11H), 4.1 (m, 2H), 3.9 (s, 3H), 3.7 (s, 3H), 3.5 (m, 2H), 3.3 (m, 2H), 2.2 (m, 2H) and 2.1 (m, 2H).

Workup

  1. customThe orange solid which precipitated
  2. filtrationwas filtered
  3. washwashed with water
  4. customdried
  5. customThe crude product was purified by silica gel chromatography (eluent: 5% methanol/DCM)

Sources & evidence

ORD record
ord-2f0e308716c141d98ad61776008d5fa0
Source dataset
uspto-grants-2008_11
Patent number
US07452873B2

Reaction notes

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