Formic Acid → HCID 13749193, compound

HRID 1732060Notes

Reaction equation

HRID 1732060 reaction equation
[CH:1]([OH:3])=O.C(OC(=O)C)(=O)C.Cl.[CH3:12][C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]2[CH2:22][CH2:23][CH2:24][CH:25]([NH2:26])[C:14]=12.O>O1CCCC1>[CH3:12][C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]2[CH2:22][CH2:23][CH2:24][CH:25]([NH:26][CH:1]=[O:3])[C:14]=12

Participants

6

Reactant 4

HCID 284Formic AcidHCID 962WaterHCID 7918Acetic AnhydrideHCID 13749167HCID 13749167, compound

Product 1

HCID 13749193HCID 13749193, compoundYield 99%

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-10-methylpyrido[1,2-a]indol-9-amine hydrochloride (7.5 g, 37.5 mmol), in dry tetrahydrofuran (60 mL) was added upon cooling to the resultant mixed anhydride. The reaction mixture was stirred at 25° C. for 2 hours, poured into water (150 mL) and extracted with ether (3×100 mL). The combined extracts were washed successively with 5% hydrochloric acid, 5% sodium bicarbonate, and water. The ethereal solution was dried over MgSO4, filtered, and evaporated. The solid residue was crystallized from benzene/hexane to give 8.5 g (99%) of the title formamide as a yellow solid, m.p. 133°-5° C. Analytical sample melted at 136° C.

Workup

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

Sources & evidence

ORD record
ord-c4ee719a9e82470087284c8e90d75672
Source dataset
uspto-grants-1986_11
Patent number
US04624954

Reaction notes

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