Hydrochloric Acid → HCID 66703851, compound

HRID 424407Notes

Reaction equation

HRID 424407 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([NH:10][C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]3=[N:21][N:22]=[C:23]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[CH3:30])[N:13]3[N:12]=2)[CH:7]=[CH:8][CH:9]=1)([O-])=O.Cl.O.O.[Sn](Cl)(Cl)(Cl)Cl>C(O)(=O)C>[CH3:30][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=1[C:23]1[N:13]2[N:12]=[C:11]([NH:10][C:6]3[CH:7]=[CH:8][CH:9]=[C:4]([NH2:1])[CH:5]=3)[C:20]3[C:15]([C:14]2=[N:21][N:22]=1)=[CH:16][CH:17]=[CH:18][CH:19]=3

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 66703859HCID 66703859, compoundHCID 85782573Tin tetrachloride dihydrate

Product 1

HCID 66703851HCID 66703851, compoundYield 84.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
90 °C

Procedure

To a suspension of (3-nitro-phenyl)-(3-o-tolyl-[1,2,4]triazolo[3,4-a]-phthalazin-6-yl)-amine (compound B10) (263 mg, 0.66 mmol) in a 2:1 mixture of glacial acetic acid and 37% hydrochloric acid (18 ml) is added tin chloride dihydrate (450 mg, 1.99 mmol). The mixture is stirred at 90° C. for 2 days. Upon cooling, the precipitate is filtered and the filtrate concentrated. Purification of residue by column chromatography (CH2Cl2/MeOH, 95:5) gives 205 mg of an off-white solid which is triturated with a 1:1 mixture of isopropanol and petroleum ether to yield 77 mg of the title compound as off-white needles.

Workup

  1. temperatureUpon cooling
  2. filtrationthe precipitate is filtered
  3. concentrationthe filtrate concentrated
  4. customPurification of residue by column chromatography (CH2Cl2/MeOH, 95:5)

Sources & evidence

ORD record
ord-ddb4ff049dfc4e6c95debb2a76f52c10
Source dataset
uspto-grants-2012_01
Patent number
US08106047B2

Reaction notes

Loading…