Formic Acid → HCID 13749174, compound

HRID 1732068Notes

Reaction equation

HRID 1732068 reaction equation
[CH:1]([OH:3])=O.C(OC(=O)C)(=O)C.[CH3:11][O:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[N:18]1[CH2:22][CH2:23][CH2:24][CH:25]([NH2:26])[C:17]1=[C:16]2[CH3:27].O>O1CCCC1>[CH3:11][O:12][C:13]1[CH:14]=[C:15]2[C:19](=[CH:20][CH:21]=1)[N:18]1[CH2:22][CH2:23][CH2:24][CH:25]([NH:26][CH:1]=[O:3])[C:17]1=[C:16]2[CH3:27]

Participants

6

Reactant 4

HCID 284Formic AcidHCID 962WaterHCID 7918Acetic AnhydrideHCID 20203559HCID 20203559, compound

Product 1

HCID 13749174HCID 13749174, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of formic acid (6 mL) and acetic anhydride (12 mL) was heated at 60° C. for 4 hours. A solution of 6,7,8,9-tetrahydro-2-methoxy-10-methylpyrido[1,2-a]indol-9-amine (5.8 g, 25.2 mmol) in dry tetrahydrofuran (60 mL) was added upon cooling to the resultant mixed anhydride. The reaction mixture was stirred at 25° C. overnight, poured into water (100 mL), and extracted with ether (3×70 mL). The combined extracts were washed successively with 5% hydrochloric acid (80 mL), 5% aqueous sodium bicarbonate (100 mL), and water (100 mL). The ethereal solution was dried over MgSO4, filtered, and evaporated. The solid residue was crystallized from ether-hexane to give 5.4 g (83%) of the title formamide, m.p. 130°-132° C. as a beige solid.

Workup

  1. temperatureupon cooling to the resultant
  2. extractionextracted with ether (3×70 mL)
  3. washThe combined extracts were washed successively with 5% hydrochloric acid (80 mL), 5% aqueous sodium bicarbonate (100 mL), and water (100 mL)
  4. dry with materialThe ethereal solution was dried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe solid residue was crystallized from ether-hexane

Sources & evidence

ORD record
ord-1206bf7cf60a4972addef22d10326144
Source dataset
uspto-grants-1986_11
Patent number
US04624954

Reaction notes

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