Dimethylformamide → 4-(Dibenzylamino)-6-methoxy-1-naphthaldehyde

HRID 889411Notes

Reaction equation

HRID 889411 reaction equation
O=P(Cl)(Cl)Cl.[CH2:6]([N:13]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([O:24][CH3:25])[CH:22]=2)[CH:17]=[CH:16][CH:15]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.CN([CH:36]=[O:37])C>>[CH2:26]([N:13]([CH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)[C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([O:24][CH3:25])[CH:22]=2)[C:17]([CH:36]=[O:37])=[CH:16][CH:15]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

4

Reactant 3

HCID 6228Dimethylformamide2×HCID 24813Phosphorus oxychlorideHCID 59813090N,N-dibenzyl-7-methoxynaphthalen-1-amine

Product 1

HCID 598131174-(Dibenzylamino)-6-methoxy-1-naphthaldehyde

Conditions

Temperature
0 °C

Procedure

To a stirred solution of DMF (30 mL) was added POCl3 (10.65 mL, 116 mmol) over 30 minutes at 0° C. The mixture was then stirred at 0° C. for 30 minutes and added 4 (11.75 g, 33.2 mmol) in DMF (120 mL). The mixture was stirred at room temperature for six days and the poured into ice-water. The product mixture was extracted with dichloromethane and the organic layer washed with water, aqueous sodium bicarbonate and brine, dried over sodium sulfate and concentrated to afford 13.58 g of 4-(dibenzylamino)-6-methoxy-1-naphthaldehyde (5) which was used in next step without further purification.

Workup

  1. stirringThe mixture was stirred at room temperature for six days
  2. extractionThe product mixture was extracted with dichloromethane
  3. washthe organic layer washed with water, aqueous sodium bicarbonate and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-de0e44ee5b7d4efea7a9eee0f1acc00a
Source dataset
uspto-grants-2012_08
Patent number
US08252828B2

Reaction notes

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