Hydroxyamine hydrochloride → HCID 178467977, compound

HRID 2278775Notes

Reaction equation

HRID 2278775 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([CH3:19])[C:9]=1[O:10][CH2:11][CH:12]([O:16][CH2:17][CH3:18])[O:13][CH2:14][CH3:15])[C:5]#[N:6].[ClH:20].[NH2:21][OH:22].C([O-])(O)=O.[Na+]>CO.CC(=O)OCC>[Cl:20][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([CH3:19])[C:9]=1[O:10][CH2:11][CH:12]([O:16][CH2:17][CH3:18])[O:13][CH2:14][CH3:15])[C:5](=[NH:6])[NH:21][OH:22]

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 70557431HCID 70557431, compound

Product 1

HCID 178467977HCID 178467977, compoundYield 87.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of 3-chloro-4-(2,2-diethoxyethoxy)-5-methylbenzonitrile (4.54 g, 16.0 mmol) in methanol (50 mL), hydroxylamine hydrochloride (3.34 g, 48.0 mmol) and NaHCO3 (2.69 g, 32.0 mmol) is added. The mixture is stirred at 75° C. for 2 h before it is diluted with EA (120 mL) and washed with water (100 mL). The washing is extracted twice with EA (2×75 mL). The combined org. extracts are dried over MgSO4, filtered and concentrated to give the title compound (4.43 g) as a beige wax which slowly solidifies upon standing; LC-MS: tR=0.55 min, [M+1]+=317.28.

Workup

  1. washwashed with water (100 mL)
  2. extractionThe washing is extracted twice with EA (2×75 mL)
  3. dry with materialextracts are dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-bd7870cb22e24040b2453dec3ab63a77
Source dataset
uspto-grants-2015_09
Patent number
US09133179B2

Reaction notes

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