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

HRID 448155Notes

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

Reactant 3

HCID 6228Dimethylformamide2×

HCID 24813Phosphorus oxychloride

HCID 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

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

Sources & evidence

ORD record: ord-fd087be93fa64e4c88e1eb9cc41befac
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08481581B2

Reaction notes

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