(2-(2-(Dimethylamino)ethylamino)-3-fluorophenyl)methanol → 2-(2-(Dimethylamino)ethylamino)-3-fluorobenzaldehyde

HRID 1695935Notes

Reaction equation

HRID 1695935 reaction equation
[CH3:1][N:2]([CH3:15])[CH2:3][CH2:4][NH:5][C:6]1[C:11]([F:12])=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:13][OH:14]>C1(C)C=CC=CC=1.O=[Mn]=O>[CH3:1][N:2]([CH3:15])[CH2:3][CH2:4][NH:5][C:6]1[C:11]([F:12])=[CH:10][CH:9]=[CH:8][C:7]=1[CH:13]=[O:14]

Participants

4

Reactant 1

HCID 57774489(2-(2-(Dimethylamino)ethylamino)-3-fluorophenyl)methanol

Product 1

HCID 577744202-(2-(Dimethylamino)ethylamino)-3-fluorobenzaldehyde

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 1140TolueneSolvent

Procedure

(2-(2-(dimethylamino)ethylamino)-3-fluorophenyl)methanol (536 mg, 2.525 mmol) and MnO2 (878.1 mg, 174.7 μL, 10.10 mmol) were heated to reflux in toluene (13 mL) overnight. The suspension was filtered through Celite with CH2Cl2 and concentrated on a rotary evaporator. The crude product was purified on 12 g Redisep ISCO column eluting with 4-55% EtOAc/Hexanes over 30 CV. 2-(2-(Dimethylamino)ethylamino)-3-fluorobenzaldehyde was identified by 1H-NMR and carried on to next reaction.

Workup

  1. filtrationThe suspension was filtered through Celite with CH2Cl2
  2. concentrationconcentrated on a rotary evaporator
  3. customThe crude product was purified on 12 g Redisep ISCO column
  4. washeluting with 4-55% EtOAc/Hexanes over 30 CV
  5. customcarried on to next reaction

Sources & evidence

ORD record
ord-05d0d4d99adb4fb5b23619958368f273
Source dataset
uspto-grants-2012_04
Patent number
US08163737B2

Reaction notes

Loading…