Sodium Hydroxide → 4-(3-Bromopropoxy)aniline

HRID 1451643Notes

Reaction equation

HRID 1451643 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12]C(=O)C)=[CH:8][CH:7]=1.[OH-].[Na+]>Cl>[Br:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10849771N-[4-(3-bromopropoxy)phenyl]acetamide

Product 1

HCID 199745634-(3-Bromopropoxy)aniline

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of the product of part (i) above (13 g) and 5N hydrochloric acid (200 ml) was heated under reflux for 2 h. After cooling, the mixture was basified with sodium hydroxide solution and extracted with dichloromethane. The organic phase was evaporated to give the title compound (7 g) as an oil. IR includes a peak at 3360-3450 cm-1 (NH).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 h
  3. temperatureAfter cooling
  4. extractionextracted with dichloromethane
  5. customThe organic phase was evaporated

Sources & evidence

ORD record
ord-844f3f95de144ec39e3629178d3a957b
Source dataset
uspto-grants-1997_02
Patent number
US05604237

Reaction notes

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