3-Nitrobenzaldehyde → Methyl 3,4,5,8,-tetrahydro-6-methyl-8-(3-nitrophenyl)-1,1-dioxo-2H-thiopyrano-[3,2-b]pyridine-7-carboxylate

HRID 231346Notes

Reaction equation

HRID 231346 reaction equation
[S:1]1(=[O:9])(=[O:8])[CH2:6][CH2:5][CH2:4][C:3](=O)[CH2:2]1.[N+:10]([C:13]1[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=1)[CH:16]=O)([O-:12])=[O:11].[NH2:21]/[C:22](/[CH3:28])=[CH:23]\[C:24]([O:26][CH3:27])=[O:25]>CO>[CH3:28][C:22]1[NH:21][C:3]2[CH2:4][CH2:5][CH2:6][S:1](=[O:9])(=[O:8])[C:2]=2[CH:16]([C:15]2[CH:18]=[CH:19][CH:20]=[C:13]([N+:10]([O-:12])=[O:11])[CH:14]=2)[C:23]=1[C:24]([O:26][CH3:27])=[O:25]

Participants

5

Reactant 3

HCID 74493-NitrobenzaldehydeHCID 643918Methyl 3-aminocrotonateHCID 11815935Dihydro-2H-thiopyran-3(4H)-one-1,1-dioxide

Product 1

HCID 14011211Methyl 3,4,5,8,-tetrahydro-6-methyl-8-(3-nitrophenyl)-1,1-dioxo-2H-thiopyrano-[3,2-b]pyridine-7-carboxylateYield 29.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of tetrahydrothiopyran-3-one-1,1-dioxide (0.830 g, 0.0056 moles), 3-nitrobenzaldehyde (0.846 g, 0.0056 moles) and methyl 3-aminocrotonate (0.644 g, 0.0056 moles) in methanol (20 mL) was refluxed for 16 hours. After cooling, the resulting solid was isolated by filtration and washed with diethyl ether. This solid was dried at 40° C. for 4 hours under vacuum to give 0.620 g product; mp 236°-238° C.

Workup

  1. temperaturewas refluxed for 16 hours
  2. temperatureAfter cooling
  3. customthe resulting solid was isolated by filtration
  4. washwashed with diethyl ether
  5. customThis solid was dried at 40° C. for 4 hours under vacuum

Sources & evidence

ORD record
ord-ea3c9fc7f1994ca0a5c0526e8875064b
Source dataset
uspto-grants-1989_07
Patent number
US04845225

Reaction notes

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