Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ammonia | HCID 222 | — |
| Reactant | Water | HCID 962 | — |
| Reactant | Methyl 5-amino-2-bromobenzoate | HCID 245495 | — |
| Reactant | HCID 178418546 | HCID 178418546 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | Methyl 5-amino-2-cyanobenzoate | HCID 53419719 | — |
Reaction Steps
The mixture of 5-amino-2-bromobenzoic acid methyl ester (14.27 g, 62.0 mmol) and CuCN (6.11 g, 68.2 mmol) in DMF (130 ml) was heated at 150° C. for 1 h 10 min under nitrogen atmosphere. The mixture was cooled to 70° C. and poured into the mixture of water (250 ml) and 12.5% NH3 (500 ml). The product was extracted into ethyl acetate (3×250 ml). The organic phase was washed several times with 12.5% NH3 and water, dried over Na2SO4 and concentrated under vacuum.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08501814B2 |
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| Source dataset | uspto-grants-2013_08 |
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| ORD ID | ord-f4a1ca1586f34ff38ef1527bc7f2ffa2 |
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| Source note | uspto-grants-2013_08 |
|---|