Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Formic Acid | HCID 284 | — |
| Reactant | Water | HCID 962 | — |
| Reactant | Acetic Anhydride | HCID 7918 | — |
| Reactant | HCID 13749175 | HCID 13749175 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 13920729 | HCID 13920729 | 95% |
Reaction Steps
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.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US04665183 |
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| Source dataset | uspto-grants-1987_05 |
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| ORD ID | ord-cf97b978422545df8717450e172efeb9 |
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| Source note | uspto-grants-1987_05 |
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