Formaldehyde → Methyl 2-dimethylamino-3-benzoylphenylacetate
Reaction equation
N[C:2]1[C:7]([C:8](=[O:15])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:16][C:17]([O:19][CH3:20])=[O:18].C=O.[C:23](#N)C.[C:26]([BH3-])#[N:27].[Na+]>CCOCC.C(O)(=O)C>[CH3:23][N:27]([CH3:26])[C:2]1[C:7]([C:8](=[O:15])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:16][C:17]([O:19][CH3:20])=[O:18]Participants
Procedure
A stirred solution of 4.6 gms. (0.0165 mole) of methyl 2-amino-3-benzoylphenylacetate and 13.2 ml. (0.165 mole) of 37% formaldehyde in 66 ml. of acetonitrile was treated with 3.14 gms. (0.0495 mole) of sodium cyanoborohydride. Glacial acetic acid (1.65 ml.) was added over a 10 minute period and stirring contained for 2.0 hrs. at room temperature. An additional 1.65 ml. of glacial acetic acid was added and the mixture stirred over a weekend (co. 65 hours). The mixture was diluted with ether and the ether solution was successively washed with 3N potassium hydroxide solution, water, dried over sodium sulfate and concentrated under vacuum to give approximately 1.0 gms. (18%) of a yellow oil. A portion of the oil was molecularly distilled for an analytical sample.
Workup
- customat room temperature
- stirringthe mixture stirred over a weekend (co. 65 hours)
- washthe ether solution was successively washed with 3N potassium hydroxide solution, water
- dry with materialdried over sodium sulfate
- concentrationconcentrated under vacuum
- customto give approximately 1.0 gms
- distillationA portion of the oil was molecularly distilled for an analytical sample
Sources & evidence
- ORD record
- ord-eb0d034585144e139acfe661b02b4752
- Source dataset
- uspto-grants-1978_11
- Patent number
- US04126635
Reaction notes
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