Sodium Carbonate → HCID 178513284, compound

HRID 1672339Notes

Reaction equation

HRID 1672339 reaction equation
[C:1]1([C:7]2[CH:16]=[CH:15][C:14]3[N:13]=[CH:12][C:11]4[N:17]=[CH:18][N:19]([C:20]5[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=5[C:22]#[N:23])[C:10]=4[C:9]=3[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[NH2:29][OH:30].C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C.O>[OH:30][NH:29][C:22](=[NH:23])[C:21]1[CH:24]=[CH:25][CH:26]=[CH:27][C:20]=1[N:19]1[C:10]2[C:9]3[CH:8]=[C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[CH:16]=[CH:15][C:14]=3[N:13]=[CH:12][C:11]=2[N:17]=[CH:18]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 10405339HCID 10405339, compound

Product 1

HCID 178513284HCID 178513284, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To 300 mg (0.832 mmol) of 2-(8-phenyl-imidazo[4,5-c]quinolin-1-yl)-benzonitrile (Example 63) and 360 mg (5.19 mmol) hydroxylamine hydrochloride in 7 ml DMF, a solution of 490 mg (4.61 mmol) sodium carbonate in 2.6 ml water is added using a syringe within 3 min. After a few minutes, a precipitate starts to appear. Stirring is continued for 4 h at 70° C. (tlc-control). The reaction mixture is cooled to 0° C. and is poured into 100 ml ice-water. The compound is filtered off, washed with water and hexane, and dried at 65° C. for 16 h (high-vacuum). mp: 249-251° C. MS: 380 (M+1); HPLC: tret=6.91 min (Grad 1).

Workup

  1. customwithin 3 min
  2. waitAfter a few minutes
  3. filtrationThe compound is filtered off
  4. washwashed with water and hexane
  5. customdried at 65° C. for 16 h (high-vacuum)
  6. customtret=6.91 min (Grad 1)

Sources & evidence

ORD record
ord-82190ebb25cc43bca77cfcb3d4014021
Source dataset
uspto-grants-2011_08
Patent number
US07998972B2

Reaction notes

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