HuagongsheHuagongshe Chemistry Print Report · For research reference only
2-Chlorobenzoyl chloride → HCID 59505264, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2-Chlorobenzoyl chloride | HCID 69110 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Methyl (1R)-1-aminoindane-5-carboxylate hydrochloride | HCID 67546135 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Solvent | Ammonium Chloride | HCID 25517 | — |
| Product | HCID 59505264 | HCID 59505264 | 74% |
Reaction Steps
(R)-Methyl 1-amino-2,3-dihydro-1H-indene-5-carboxylate hydrochloride (A-02) (0.661 mmol, 1 eq) was dissolved in dichloromethane and DIPEA (2.5 eq) under a protecting gas atmosphere, and 2-chlorobenzoic acid chloride (1 eq) was added at 0° C. The reaction mixture was stirred for 2 h at RT. Then the reaction mixture was diluted with 10% ammonium chloride solution and ethyl acetate, and the phases were separated. The organic phase was washed with sat. NaCl solution, dried over magnesium sulfate and concentrated. The crude product was purified by column chromatography (silica gel, cyclohexane:ethyl acetate 2:1) to yield (R)-methyl 1-(2-chlorobenzamido)-2,3-dihydro-1H-indene-5-carboxylate (B-02). Yield: 74%
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08680159B2 |
| Source dataset | uspto-grants-2014_03 |
| ORD ID | ord-3e3549bb49a64e75a071f6ab72a00bf6 |
| Source note | uspto-grants-2014_03 |