Sodium Carbonate → HCID 178513394, compound

HRID 1672348Notes

Reaction equation

HRID 1672348 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6]3[N:12]=[C:13]([C:22]#[N:23])[N:14]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=4[Cl:21])[C:5]=3[C:4]=2[CH:3]=1.Cl.[NH2:25][OH:26].C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.O>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6]3[N:12]=[C:13]([C:22]([NH:25][OH:26])=[NH:23])[N:14]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=4[Cl:21])[C:5]=3[C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 10449844HCID 10449844, compound

Product 1

HCID 178513394HCID 178513394, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a mixture of 300 mg of (0.884 mmol) 8-chloro-1-(2-chloro-phenyl)-1H-imidazo[4,5-c]quinoline-2-carbonitrile (Example 84) and 245 mg (3.537 mmol) hydroxylamine hydrochloride in 7.5 ml DMF, a solution of 326 mg (3.08 mmol) sodium carbonate in 1.8 ml water is added by syringe within 2 min. The reaction mixture is heated at 70° C. for 4½ h. The cold solution is poured in ice-water and stirred for 1 h. The precipitate which is formed is filtered off and washed with water and ethanol. The compound is dried over night at 60° C. (high vacuum). mp: 265-267° C.; MS: 372 (M++1); HPLC: tret=80.43 min (Grad 1).

Workup

  1. customThe precipitate which is formed
  2. filtrationis filtered off
  3. washwashed with water and ethanol
  4. customThe compound is dried over night at 60° C. (high vacuum)
  5. customtret=80.43 min (Grad 1)

Sources & evidence

ORD record
ord-7824d8975ba1402b953585ed6bf13be9
Source dataset
uspto-grants-2011_08
Patent number
US07998972B2

Reaction notes

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