Sodium Carbonate → HCID 178489480, compound

HRID 1669728Notes

Reaction equation

HRID 1669728 reaction equation
[CH3:1][O:2][C:3]1[CH:22]=[CH:21][CH:20]=[CH:19][C:4]=1[CH2:5][NH:6][C:7]1[CH:16]=[CH:15][C:14]2[C:13]([C:17]#[N:18])=[CH:12][CH:11]=[CH:10][C:9]=2[N:8]=1.Cl.[NH2:24][OH:25].C(=O)([O-])[O-].[Na+].[Na+]>C(O)C.O>[OH:25][NH:24][C:17]([C:13]1[C:14]2[CH:15]=[CH:16][C:7]([NH:6][CH2:5][C:4]3[CH:19]=[CH:20][CH:21]=[CH:22][C:3]=3[O:2][CH3:1])=[N:8][C:9]=2[CH:10]=[CH:11][CH:12]=1)=[NH:18]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 67332820HCID 67332820, compound

Product 1

HCID 178489480HCID 178489480, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A stirred suspension of 2-(2-methoxy-benzylamino)-quinoline-5-carbonitrile (example 136, step B) (289 mg, 1.0 mmol), hydroxylamine hydrochloride (257 mg, 3.7 mmol) and sodium carbonate (212 mg, 2.0 mmol) in ethanol (4 ml) and water (4 ml) was heated under reflux conditions for 17 h, water (5 ml) was added, the precipitate was collected by filtration, washed with water and heptane and dried to yield the crude product as solid which was further purified by crystallization (diethyl ether/ methanol) to yield N-hydroxy-2-(2-methoxy-benzylamino)-quinoline-5-carboxamidine as off-white solid (290 mg, 90%). MS (ISP): m/e=323.2 (M+H+); m.p. 161° C.

Workup

  1. temperaturewas heated under reflux conditions for 17 h
  2. filtrationthe precipitate was collected by filtration
  3. washwashed with water and heptane
  4. customdried
  5. customto yield the crude product as solid which
  6. customwas further purified by crystallization (diethyl ether/ methanol)

Sources & evidence

ORD record
ord-3caf947850804af3a99dc54c4b19dec3
Source dataset
uspto-grants-2011_08
Patent number
US07989628B2

Reaction notes

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