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

HRID 1675488Notes

Reaction equation

HRID 1675488 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-be6d4b97b94d4ceda787a65c7652a79a
Source dataset
uspto-grants-2011_08
Patent number
US08003681B2

Reaction notes

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