Sodium Hydroxide → 2-(4-Chlorophenoxy)benzenemethanamine hydrochloride

HRID 1612794Notes

Reaction equation

HRID 1612794 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:22]=[CH:21][C:11]([O:12][C:13]2[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=2[C:15]#[N:16])=[CH:10][CH:9]=1.[OH-].[Na+]>O1CCCC1>[ClH:7].[Cl:7][C:8]1[CH:22]=[CH:21][C:11]([O:12][C:13]2[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=2[CH2:15][NH2:16])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 141307012-(4-Chlorophenoxy)benzonitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 199266692-(4-Chlorophenoxy)benzenemethanamine hydrochlorideYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 51.4 g of 4-chlorophenol in 500 ml of dry N,N-dimethylformamide (DMF) was added to a suspension of 20 g of 60% sodium hydride in 800 ml of dry DMF under nitrogen. After 30 min at 25° C., 1 g of 18-crown-6 was added. After the addition of 73 g of 2-bromobenzonitrile in 500 ml of dry DMF, the mixture was heated at 100° C. for 16 h. After concentration in vacuo, 2 N sodium hydroxide and ethyl acetate were added. The organic layer was separated, washed with 2 N sodium hydroxide and water, dried over magnesium sulfate, and evaporated to dryness. The residue was recrystallized from methanol to give in 60% yield 2-(4-chlorophenoxy)benzonitrile. To a suspension of 6 g of lithium aluminum hydride in 100 ml of dry tetrahydrofuran (THF) were added under nitrogen 20 of 2-(4-chlorophenoxy)benzonitrile. The mixture was heated at reflux for 3 h, cooled, and 25 ml of 1 N sodium hydroxide were added dropwise. The precipitate formed was filtered off and washed with diethyl ether. The filtrate was evaporated to dryness, dissolved in ethyl acetate and acidified with a saturated solution of hydrochloric acid in ethanol. The precipitate was collected and recrystallized from ethanol to give in 95% yield 2-(4-chlorophenoxy)benzenemethanamine hydrochloride. mp 253° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 3 h
  3. temperaturecooled
  4. customThe precipitate formed
  5. filtrationwas filtered off
  6. washwashed with diethyl ether
  7. customThe filtrate was evaporated to dryness
  8. dissolutiondissolved in ethyl acetate
  9. customThe precipitate was collected
  10. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-e7d3a32d012c4d9eaeb005041316250a
Source dataset
uspto-grants-1993_03
Patent number
US05190965

Reaction notes

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