Water → HCID 21098408, compound

HRID 1351182Notes

Reaction equation

HRID 1351182 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:24][CH3:25])=[C:16]([O:22][CH3:23])[C:17]=3[N+:19]([O-])=O)[N:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1.[NH4+].[Cl-].O.C(Cl)(Cl)Cl>CO.[Zn]>[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:18]3[C:17]([NH2:19])=[C:16]([O:22][CH3:23])[C:15]([O:24][CH3:25])=[CH:14][C:13]=3[N:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6212ChloroformHCID 25517Ammonium ChlorideHCID 21098388HCID 21098388, compound

Product 1

HCID 21098408HCID 21098408, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Procedure

To a solution of (3-chloro-phenyl)-(6,7-dimethoxy-5-nitro-quinazolin-4-yl)-amine (0.2 g, 0.55 mmol) (from Example 11, Step A, supra) and NH4Cl (0.24 g, 4.43 mmol) in a mixture of MeOH, H2O and CHCl3 (50 mL, 2:1:12), was added Zn powder (0.72 g, 11 mmol). The reaction mixture was stirred at room temperature for 3 hours. The mixture was then filtered. The filtrate was concentrated and then extracted with chloroform (100 mL). The organic layer was separated, dried over Na2SO4, and concentrated. The residue was purified by chromatography using EtOAc/CH2Cl2 /NEt3 (1:1:0.05) as eluent to give the desired N4-(3-chloro-phenyl)-6,7-dimethoxy-quinazoline-4,5-diamine as an orange gum. (Yield 0.1 g, 55%).

Workup

  1. filtrationThe mixture was then filtered
  2. concentrationThe filtrate was concentrated
  3. extractionextracted with chloroform (100 mL)
  4. customThe organic layer was separated
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-13cffa07f2a0400abcf0c240682eb0ca
Source dataset
uspto-grants-2007_05
Patent number
US07217717B2

Reaction notes

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