Benzenamine, 3-chloro-, hydrochloride (1:1) → HCID 178526611, compound

HRID 1602252Notes

Reaction equation

HRID 1602252 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][CH:9]=1)[NH2:6].[N+:10]([C:13]1[CH:14]=[C:15]([C:19]2[C:23](C#N)=[C:22]([N:26]=[CH:27][N:28]([CH3:30])C)[NH:21][N:20]=2)[CH:16]=[CH:17][CH:18]=1)([O-:12])=[O:11]>CO>[Cl:2][C:3]1[CH:4]=[C:5]([NH:6][C:30]2[N:28]=[CH:27][N:26]=[C:22]3[NH:21][N:20]=[C:19]([C:15]4[CH:16]=[CH:17][CH:18]=[C:13]([N+:10]([O-:12])=[O:11])[CH:14]=4)[C:23]=23)[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 67336Benzenamine, 3-chloro-, hydrochloride (1:1)HCID 178484261HCID 178484261, compound

Product 1

HCID 178526611HCID 178526611, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

With the exclusion of air, 172.2 mg (1.05 mmol) of 3-chloro-aniline hydrochloride (see Step 14.4) are added to 199 mg (0.70 mmol) of N'-[3-(3-nitro-phenyl)-4-cyano-1H-pyrazol-5-yl]-N,N-dimethylformamidine in 2 ml of methanol and the reaction mixture is boiled under reflux for 19 hours. Cooling, filtering and washing with isopropanol and hexane yield 4-(3-chloro-phenylamino)-3-(3-nitro-phenyl)-1H-pyrazolo[3,4-d]pyrimidine; TLC: Rt=0.55 (methylene chloride:methanol=10:1); HPLC: TRet (Grad20-100)=14.2; 1H-NMR: (DMSO-d6) 9.05 (s, HN), 8.54 (s, 2H), 8.32 (dd, J=8, 2, 1H), 8.22 (d, J=8, 1H), 7.8 (m, 2H), 7.49 (d, J=8, 1H), 7.33 (t, J=8, 1H), 7.10 (dd, J=8, 2, 1H).

Workup

  1. temperatureunder reflux for 19 hours
  2. temperatureCooling
  3. filtrationfiltering
  4. washwashing with isopropanol and hexane

Sources & evidence

ORD record
ord-7b50e89238e24379be5d52706f259eaf
Source dataset
uspto-grants-1999_11
Patent number
US05981533

Reaction notes

Loading…