Formic Acid → HCID 13749193, compound
Reaction equation
[CH:1]([OH:3])=O.CC(OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=O.Cl.[CH3:29][C:30]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[N:32]2[CH2:39][CH2:40][CH2:41][CH:42]([NH2:43])[C:31]=12.O>O1CCCC1>[CH3:29][C:30]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[N:32]2[CH2:39][CH2:40][CH2:41][CH:42]([NH:43][CH:1]=[O:3])[C:31]=12Participants
Conditions
- Temperature
- 60 °C
Procedure
A mixture of formic acid (b 6 mL) and acetic anhyride (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
- temperatureupon cooling to the resultant
- extractionextracted with ether (3×100 mL)
- washThe combined extracts were washed successively with 5% hydrochloric acid, 5% sodium bicarbonate, and water
- dry with materialThe ethereal solution was dried over MgSO4
- filtrationfiltered
- customevaporated
- customThe solid residue was crystallized from benzene/hexane
Sources & evidence
- ORD record
- ord-164237aad1c94d159c8928e996a3da1b
- Source dataset
- uspto-grants-1987_05
- Patent number
- US04665183
Reaction notes
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