Formic Acid → HCID 13920729, compound

HRID 1732069Notes

Reaction equation

HRID 1732069 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]([NH:26][CH3:27])[C:17]1=[C:16]2[CH3:28].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]([N:26]([CH3:27])[CH:1]=[O:3])[C:17]1=[C:16]2[CH3:28]

Participants

6

Reactant 4

HCID 284Formic AcidHCID 962WaterHCID 7918Acetic AnhydrideHCID 13749175HCID 13749175, compound

Product 1

HCID 13920729HCID 13920729, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of formic acid (3.05 g, 66.3 mmol) and acetic anhydride (5.4 g, 55 mmol) was heated at 60° C. for 4 hours. A solution of 6,7,8,9-tetrahydro-2-methoxy-N,10-dimethylpyrido[1,2-a]indol-9-amine (2 g, 8.2 mmol, described in Example 27) in dry tetrahydrofuran (20 mL) was added upon cooling to the resultant mixed anhydride. The reaction mixture was stirred at 25° C. overnight, poured into water (40 mL), and extracted with ether (3×40 mL). The combined extracts were washed successively with 5% hydrochloric acid (50 mL), 5% aqueous sodium bicarbonate (60 mL), and water (80 mL). The ethereal solution was dried over MgSO4, filtered, and evaporated to afford 2.1 g (95%) of the title formamide as a yellow oil.

Workup

  1. temperatureupon cooling to the resultant
  2. extractionextracted with ether (3×40 mL)
  3. washThe combined extracts were washed successively with 5% hydrochloric acid (50 mL), 5% aqueous sodium bicarbonate (60 mL), and water (80 mL)
  4. dry with materialThe ethereal solution was dried over MgSO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-d772bea0456348f19b9d23138059bf58
Source dataset
uspto-grants-1986_11
Patent number
US04624954

Reaction notes

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