Formic Acid → HCID 86740815, compound

HRID 280570Notes

Reaction equation

HRID 280570 reaction equation
[C:1](OC=O)(=[O:3])C.C(O)=O.C(OC(=O)C)(=O)C.[NH2:17][CH2:18][CH2:19][O:20][CH2:21][C:22]1[NH:23][C:24]([CH3:45])=[C:25]([C:41]([O:43][CH3:44])=[O:42])[CH:26]([C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([Cl:39])[C:34]=2[Cl:40])[C:27]=1[C:28]([O:30][CH2:31][CH3:32])=[O:29]>O1CCCC1>[Cl:40][C:34]1[C:35]([Cl:39])=[CH:36][CH:37]=[CH:38][C:33]=1[CH:26]1[C:25]([C:41]([O:43][CH3:44])=[O:42])=[C:24]([CH3:45])[NH:23][C:22]([CH2:21][O:20][CH2:19][CH2:18][NH:17][CH:1]=[O:3])=[C:27]1[C:28]([O:30][CH2:31][CH3:32])=[O:29]

Participants

6

Reactant 4

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 75269Acetic-formic anhydrideHCID 13663190HCID 13663190, compound

Product 1

HCID 86740815HCID 86740815, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Formic acetic anhydride (15 ml; prepared by heating a mixture of formic acid (5 ml) and acetic anhydride (10 ml) at 50°-60° C. for 1 hour) was added over 10 minutes to a stirred, ice-cooled solution of 2-(2-aminoethoxymethyl)-4-(2,3-dichlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine (4.4 g) in tetrahydrofuran (30 ml). The mixture was stirred at room temperature for 1.5 hours and then evaporated. The residue was dissolved in dichloromethane and the solution washed with 10% aqueous sodium carbonate solution, dried (Na2SO4), and evaporated. The residual solid was collected, washed with diethyl ether and dried to give the title compound as a hemihydrate (4.0 g), m.p. 178°-181° C. Found: C, 52.69; H, 5.05; N, 6.06. C21H24Cl2N2O6.0.5H2O requires C, 52.51; H, 5.25; N, 5.83%.

Workup

  1. customprepared
  2. temperatureby heating
  3. additionwas added over 10 minutes to a stirred, ice-
  4. customevaporated
  5. dissolutionThe residue was dissolved in dichloromethane
  6. washthe solution washed with 10% aqueous sodium carbonate solution
  7. dry with materialdried (Na2SO4)
  8. customevaporated
  9. customThe residual solid was collected
  10. washwashed with diethyl ether
  11. customdried

Sources & evidence

ORD record
ord-7eec42167f9444f4b55fa55888221e11
Source dataset
uspto-grants-1986_05
Patent number
US04590195

Reaction notes

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