Ammonium Chloride → HCID 68460429, compound

HRID 269777Notes

Reaction equation

HRID 269777 reaction equation
[Cl-].[NH4+].[Cl:3][C:4]1[CH:5]=[C:6]([NH:17][C:18]2[C:27]3[C:22](=[CH:23][C:24]([N:31]4[CH2:36][CH2:35][CH:34]([N:37]5[CH2:41][CH2:40][CH2:39][CH2:38]5)[CH2:33][CH2:32]4)=[C:25]([N+:28]([O-])=O)[CH:26]=3)[N:21]=[CH:20][C:19]=2[C:42]#[N:43])[CH:7]=[CH:8][C:9]=1[S:10][C:11]1[N:12]([CH3:16])[CH:13]=[CH:14][N:15]=1.C(=O)(O)[O-].[Na+]>[Fe].O>[NH2:28][C:25]1[CH:26]=[C:27]2[C:22](=[CH:23][C:24]=1[N:31]1[CH2:32][CH2:33][CH:34]([N:37]3[CH2:38][CH2:39][CH2:40][CH2:41]3)[CH2:35][CH2:36]1)[N:21]=[CH:20][C:19]([C:42]#[N:43])=[C:18]2[NH:17][C:6]1[CH:7]=[CH:8][C:9]([S:10][C:11]2[N:12]([CH3:16])[CH:13]=[CH:14][N:15]=2)=[C:4]([Cl:3])[CH:5]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 516892Sodium BicarbonateHCID 68458639HCID 68458639, compound

Product 1

HCID 68460429HCID 68460429, compoundYield 100.3%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

To a refluxing mixture of 0.5 g (8.95 mmol) of iron powder, 0.7 g (13.1 mmol) of ammonium chloride and 14 mL of water is added 1.26 g (2.14 mmol) of 4-({3-chloro-4-[(1-methyl-1H-imidazole-2-yl)thio]phenyl}amino)-6-nitro-7-(4-pyrrolidin-1-ylpiperidin-1-yl)quinoline-3-carbonitrile in portions so as to maintain gentle reflux. The resulting mixture is heated under reflux for 45 minutes. The mixture is filtered hot through a pad of Celite, washed with ethanol, and the filtrate is evaporated to dryness to yield a residue. A saturated solution of sodium bicarbonate is added to the residue, and the mixture is stirred. The solid is collected by filtration, washed with water and dried to yield 1.2 g of 6-amino-4-[3-chloro-4-(1-methyl-1H-imidazole-2-ylsulfanyl)phenylamino]-7-(4-pyrrolidin-1-yl-piperidin-1-yl)quinoline-3-carbonitrile as a yellow solid, mp 265-267° C.

Workup

  1. temperatureto maintain gentle reflux
  2. temperatureThe resulting mixture is heated
  3. temperatureunder reflux for 45 minutes
  4. filtrationThe mixture is filtered hot through a pad of Celite
  5. washwashed with ethanol
  6. customthe filtrate is evaporated to dryness
  7. customto yield a residue
  8. filtrationThe solid is collected by filtration
  9. washwashed with water
  10. customdried

Sources & evidence

ORD record
ord-9920d8413aff4ff2ad19124172c0241c
Source dataset
uspto-grants-2008_11
Patent number
US07449460B2

Reaction notes

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