Formic Acid → HCID 13749180, compound

HRID 1732073Notes

Reaction equation

HRID 1732073 reaction equation
[CH:1]([OH:3])=O.C(OC(=O)C)(=O)C.[CH3:11][O:12][C:13]1[CH:21]=[C:20]2[C:16]([C:17]([CH3:27])=[C:18]3[CH:25]([NH2:26])[CH2:24][CH2:23][CH2:22][N:19]32)=[CH:15][CH:14]=1.O>O1CCCC1>[CH3:11][O:12][C:13]1[CH:21]=[C:20]2[C:16]([C:17]([CH3:27])=[C:18]3[CH:25]([NH:26][CH:1]=[O:3])[CH2:24][CH2:23][CH2:22][N:19]32)=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 284Formic AcidHCID 962WaterHCID 7918Acetic AnhydrideHCID 20203546HCID 20203546, compound

Product 1

HCID 13749180HCID 13749180, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of formic acid (8.5 g,) and acetic anhydride (15.2 g) was heated to 60° C. for 4 hours, then cooled to 0° C. A solution of 6,7,8,9-tetrahydro-3-methoxy-10-methylpyrido[1,2-a]indol-9-amine (6.1 g, 26.6 mmol) in tetrahydrofuran (50 mL) was added at 0° C. The reaction mixture was stirred at 0° C. for 3 hours under exclusion of moisture. It was then poured into water (75 mL) and extracted with ether (3×100 mL). The combined organic layers were washed with 5% hydrochloric acid (50 mL), and then with saturated sodium bicarbonate (3×50 mL). The separated organic layer was dried over MgSO4, filtered, and evaporated to afford 5.25 g (77%) of the title compound as an off white solid, m.p. 181°-182.5° C.

Workup

  1. temperaturecooled to 0° C
  2. extractionextracted with ether (3×100 mL)
  3. washThe combined organic layers were washed with 5% hydrochloric acid (50 mL)
  4. dry with materialThe separated organic layer was dried over MgSO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-8636ad9933b64f7482666b3579959c86
Source dataset
uspto-grants-1986_11
Patent number
US04624954

Reaction notes

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