Dimethylformamide dimethyl acetal → HCID 178496951, compound

HRID 989338Notes

Reaction equation

HRID 989338 reaction equation
[NH2:1][C:2]1[C:3]([C:14]([O:16][CH3:17])=[O:15])=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[C:7]([O:12][CH3:13])[CH:6]=2.CO[CH:20](OC)[N:21]([CH3:23])[CH3:22]>>[CH3:20][N:21](/[CH:23]=[N:1]/[C:2]1[C:3]([C:14]([O:16][CH3:17])=[O:15])=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[C:7]([O:12][CH3:13])[CH:6]=2)[CH3:22]

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 21956496Methyl 3-amino-7-methoxy-2-naphthoate

Product 1

HCID 178496951HCID 178496951, compound

Procedure

A suspension of 1.2 g (5.2 mmol) of methyl 3-amino-7-methoxy-2-naphthoate in 30 mL of dimethylformamide dimethylacetal is refluxed for 2.5 hours. The mixture is cooled to room temperature. The resulting precipitate is collected by filtration and washed with ether. After drying in vacuo, this yields 1.28 g (85.9%) of methyl 3-{[(E)-(dimethylamino)methylidene]amino}-7-methoxy-2-naphthoate as a light yellow solid, mp 160-162° C.

Workup

  1. temperatureis refluxed for 2.5 hours
  2. filtrationThe resulting precipitate is collected by filtration
  3. washwashed with ether
  4. customAfter drying in vacuo

Sources & evidence

ORD record
ord-6f854f7f901b446ca0a290e312cdf176
Source dataset
uspto-grants-2003_10
Patent number
US06638929B2

Reaction notes

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