Dimethylformamide dimethyl acetal → HCID 178468532, compound

HRID 2213801Notes

Reaction equation

HRID 2213801 reaction equation
[NH2:1][C:2]1[C:3]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([O:12][CH3:13])=[C:7]([O:14][CH2:15][CH2:16][Cl:17])[CH:6]=2.[NH2:23][C:24]1[C:25]([C:40]([O:42][CH2:43][CH3:44])=[O:41])=[CH:26][C:27]2[C:32]([CH:33]=1)=[CH:31][C:30]([O:34][CH2:35][CH2:36][Cl:37])=[C:29]([O:38][CH3:39])[CH:28]=2.CO[CH:47](OC)[N:48]([CH3:50])[CH3:49]>>[Cl:37][CH2:36][CH2:35][O:34][C:30]1[CH:31]=[C:32]2[C:27](=[CH:28][C:29]=1[O:38][CH3:39])[CH:26]=[C:25]([C:40]([O:42][CH2:43][CH3:44])=[O:41])[C:24](/[N:23]=[CH:47]/[N:48]([CH3:50])[CH3:49])=[CH:33]2.[Cl:17][CH2:16][CH2:15][O:14][C:7]1[CH:6]=[C:5]2[C:10]([CH:11]=[C:2](/[N:1]=[CH:47]/[N:48]([CH3:50])[CH3:49])[C:3]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:4]2)=[CH:9][C:8]=1[O:12][CH3:13]

Participants

5

Reactant 3

HCID 78373Dimethylformamide dimethyl acetalHCID 9858408Ethyl 3-amino-7-(2-chloroethoxy)-6-methoxy-2-naphthoateHCID 11594979Ethyl 3-amino-6-(2-chloroethoxy)-7-methoxy-2-naphthoate

Product 2

HCID 178468532HCID 178468532, compoundHCID 178468534HCID 178468534, compound

Procedure

A 648 mg portion of ethyl 3-amino-7-(2-chloroethoxy)-6-methoxy-2-naphthoate and ethyl 3-amino-6-(2-chloroethoxy)-7-methoxy-2-naphthoate (1:1 mixture) and 5 mL of dimethylformamide dimethylacetal is heated to reflux using an oil bath. The reaction is kept at reflux overnight. Solvent is removed in vacuo to provide crude ethyl 6-(2-chloroethoxy)-3-{[(E)-(dimethylamino)methylidene]amino}-7-methoxy-2-naphthoate and ethyl 7-(2-chloroethoxy)-3-{[(E)-(dimethylamino)-methylidene]amino}-6-methoxy-2-naphthoate (1:1 mixture) as a dark red mixture.

Workup

  1. temperatureto reflux
  2. temperatureat reflux overnight
  3. customSolvent is removed in vacuo

Sources & evidence

ORD record
ord-98c71b6d1e324af88dd3b6f49fb63ff7
Source dataset
uspto-grants-2006_09
Patent number
US07105531B2

Reaction notes

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