Hydroxyamine hydrochloride → HCID 45381094, compound

HRID 1402801Notes

Reaction equation

HRID 1402801 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:5]2[N:6]3[C:12](=[O:13])[CH2:11][CH:10]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[CH2:9][C:7]3=[N:8][C:4]=2[CH:3]=1.ClC1C=CC2N=C3CC(C4C=CC=CC=4)CC(=O)N3C=2C=1.[NH2:43][OH:44].[ClH:45].C([O-])C.[Na+]>C(O)C.O>[Cl:1][C:2]1[CH:21]=[CH:20][C:5]2[N:6]=[C:7]([CH2:9][CH:10]([C:14]3[CH:19]=[CH:18][C:17]([Cl:45])=[CH:16][CH:15]=3)[CH2:11][C:12]([NH:43][OH:44])=[O:13])[NH:8][C:4]=2[CH:3]=1

Participants

7

Reactant 4

HCID 443297Hydroxyamine hydrochlorideHCID 2723922Sodium ethoxideHCID 66759663HCID 66759663, compoundHCID 66760151HCID 66760151, compound

Product 1

HCID 45381094HCID 45381094, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

The above mentioned regioisomeric mixture of 7-chloro-3-phenyl-3,4-dihydropyrido[1,2-a]benzimidazol-1(2H)-one and 8-chloro-3-phenyl-3,4-dihydropyrido[1,2-a]benzimidazol-1(2H)-one (331 mg) and hydroxylamine•HCl (83 mg) in ethanol (2 ml) was heated to reflux with stirring. Sodium ethanolate (82 mg) was added to give a clear solution. Refluxing was continued for 1 h whereupon a new precipitate is formed. Water (2 ml) was added and the mixture was kept at rt overnight. The solid was isolated by suction filtration and washed with water. After drying in vacuo 4-(5-chloro-2-benzimidazolyl)-3-(4-chlorophenyl)butyrohydroxamic acid (242 mg) is obtained as light red solid.

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. customto give a clear solution
  4. temperatureRefluxing
  5. customis formed
  6. waitthe mixture was kept at rt overnight
  7. customThe solid was isolated by suction filtration
  8. washwashed with water
  9. dry with materialAfter drying in vacuo 4-(5-chloro-2-benzimidazolyl)-3-(4-chlorophenyl)butyrohydroxamic acid (242 mg)
  10. customis obtained as light red solid

Sources & evidence

ORD record
ord-3db45a63fd8e4221b41479ed9e0b3bdb
Source dataset
uspto-grants-2014_12
Patent number
US08912186B2

Reaction notes

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