Water → HCID 59211318, compound

HRID 422889Notes

Reaction equation

HRID 422889 reaction equation
[N+]([CH:4](C1C=CC=CC=1)[C:5](NC1C=CC=CC=1)=[O:6])([O-])=O.[OH:20][C:21]1[CH:22]=[C:23]([NH:27][C:28](=O)[CH2:29][C:30]2[CH:35]=[CH:34][C:33]([N+:36]([O-:38])=[O:37])=[CH:32][CH:31]=2)[CH:24]=[CH:25][CH:26]=1.B.O>O1CCCC1>[N+:36]([C:33]1[CH:34]=[CH:35][C:30]([CH2:29][CH2:28][N:27]([C:23]2[CH:24]=[CH:25][CH:26]=[C:21]([OH:20])[CH:22]=2)[C:5](=[O:6])[CH3:4])=[CH:31][CH:32]=1)([O-:38])=[O:37]

Participants

6

Reactant 4

HCID 962Water2×HCID 6331BoraneHCID 309690HCID 309690, compoundHCID 86615599HCID 86615599, compound

Product 1

HCID 59211318HCID 59211318, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

10 g (0.4 mol) of the nitrophenylacetanilide prepared in 1a) was placed in a flask and borane in tetrahydrofuran (THF) (1 M, 250 ml) was added carefully. The resulting solution was heated under reflux and water (12 ml) in THF (100 ml) was added dropwise over 1 hour. A further 50 ml of water was added and the mixture was heated for 15 mins. The THF was evaporated under reduced pressure and methanol (100 ml) was added to dissolve the oil. Thin layer chromatography (tlc)(silica H. 2 0% methanol in chloroform) gave a Rf much higher than the starting acetanilide.

Workup

  1. customwas placed in a flask
  2. temperatureThe resulting solution was heated
  3. temperatureunder reflux
  4. temperaturethe mixture was heated for 15 mins
  5. customThe THF was evaporated under reduced pressure and methanol (100 ml)
  6. additionwas added
  7. dissolutionto dissolve the oil

Sources & evidence

ORD record
ord-f233b75faa0f4c2dabadfb839adb6434
Source dataset
uspto-grants-2012_01
Patent number
US08101655B2

Reaction notes

Loading…