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 ten 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 3 N potassium solution, water, dried over sodium sulfate and concentrated under vacuum to give approximately 1.0 gm. (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 3 N potassium solution, water
- dry with materialdried over sodium sulfate
- concentrationconcentrated under vacuum
- customto give approximately 1.0 gm
- distillationA portion of the oil was molecularly distilled for an analytical sample
Sources & evidence
- ORD record
- ord-dba5fd8334424bf1b232f1aaa08dc30e
- Source dataset
- uspto-grants-1980_01
- Patent number
- US04182774
Reaction notes
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