Potassium Carbonate → Methyl 7-(4-((4-chlorophenethyl)carbamoyl)-2-nitrophenoxy)-6-chlorochroman-4-carboxylate

HRID 1021383Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[OH:12])[O:8][CH2:7][CH2:6][CH:5]2[C:13]([O:15][CH3:16])=[O:14].C([O-])([O-])=O.[K+].[K+].[Cl:23][C:24]1[CH:44]=[CH:43][C:27]([CH2:28][CH2:29][NH:30][C:31](=[O:42])[C:32]2[CH:37]=[CH:36][C:35](Cl)=[C:34]([N+:39]([O-:41])=[O:40])[CH:33]=2)=[CH:26][CH:25]=1>CS(C)=O>[Cl:23][C:24]1[CH:25]=[CH:26][C:27]([CH2:28][CH2:29][NH:30][C:31]([C:32]2[CH:37]=[CH:36][C:35]([O:12][C:11]3[CH:10]=[C:9]4[C:4]([CH:5]([C:13]([O:15][CH3:16])=[O:14])[CH2:6][CH2:7][O:8]4)=[CH:3][C:2]=3[Cl:1])=[C:34]([N+:39]([O-:41])=[O:40])[CH:33]=2)=[O:42])=[CH:43][CH:44]=1

Participants

Conditions

Temperature: 62 °C

Procedure

Methyl 6-chloro-7-hydroxychroman-4-carboxylate (100 mg, 0.412 mmol) (Preparation 4, substituting methanol for ethanol in Step C) was diluted with DMSO (1 mL) followed by the addition of K2CO3 (68.3 mg, 0.495 mmol) and N-(4-chlorophenethyl)-4-chloro-3-nitrobenzamide (140 mg, 0.412 mmol). The reaction was heated to 62° C. and stirred for 3 hours. The reaction was cooled, loaded directly onto silica gel and eluted with 5% ethyl acetate/hexanes to 100% ethyl acetate to yield methyl 7-(4-((4-chlorophenethyl)carbamoyl)-2-nitrophenoxy)-6-chlorochroman-4-carboxylate (60 mg, 26.7% yield).

Workup

temperatureThe reaction was cooled
washeluted with 5% ethyl acetate/hexanes to 100% ethyl acetate

Sources & evidence

ORD record: ord-ae5673de7aac404c85f0a9daf7a4d920
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08716498B2

Reaction notes

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