Formic Acid → HCID 18976443, compound

HRID 2393579Notes

Reaction equation

HRID 2393579 reaction equation
[NH2:1][CH:2]1[CH2:11][CH2:10][C:9]2[C:4](=[C:5]([O:15][CH3:16])[CH:6]=[CH:7][C:8]=2[O:12][CH2:13][CH3:14])[CH2:3]1.[C:17](C1NC=CN=1)(C1NC=CN=1)=[O:18].C(O)=O.CO>C1COCC1.C(OCC)(=O)C.C(Cl)Cl>[CH:17]([NH:1][CH:2]1[CH2:11][CH2:10][C:9]2[C:4](=[C:5]([O:15][CH3:16])[CH:6]=[CH:7][C:8]=2[O:12][CH2:13][CH3:14])[CH2:3]1)=[O:18]

Participants

8

Reactant 4

HCID 284Formic AcidHCID 887MethanolHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 18976427HCID 18976427, compound

Product 1

HCID 18976443HCID 18976443, compound

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

As in example 6g, 2-amino-5-ethoxy-8-methoxytetralin 408 mg (1.84 mmol) in 20 ml THF, was formylated with 360 mg (2.21 mmol) carbonyl dimidazole in 10 ml THF and 102 mg (2.21 mmol) formic acid in 3 ml THF. After stirring overnight, tlc analysis (silica gel; 10:90 CH3OH:CH2Cl2) indicated a major component, Rf 0.53, and absence of starting amine, Rf 0.06. The residue obtained on removal of solvent was dissolved in ethyl acetate, washed with 3N HCl, Na2CO3 solution, brine and dried (MgSO4). Filtration and removal of solvent in vacuo left an off-white solid, 460 mg (100%).

Workup

  1. customThe residue obtained on removal of solvent
  2. washwashed with 3N HCl, Na2CO3 solution, brine
  3. dry with materialdried (MgSO4)
  4. filtrationFiltration and removal of solvent in vacuo
  5. waitleft an off-white solid, 460 mg (100%)

Sources & evidence

ORD record
ord-f6854839e2fd43a7acd11de22ff6521c
Source dataset
uspto-grants-1998_09
Patent number
US05807897

Reaction notes

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