Acetic Acid → HCID 59259056, compound

HRID 641837Notes

Reaction equation

HRID 641837 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][C:10]#[CH:11])=[CH:4][C:3]=1[C:12]([C:14]1[CH:19]=[CH:18][C:17]([CH:20]2[CH2:22][CH2:21]2)=[CH:16][CH:15]=1)=[O:13].[CH:23](=O)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.CC(O)=O.C([BH3-])#N.[Na+]>CO.C(OCC)(=O)C.O>[CH2:23]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:9][C:10]#[CH:11])=[CH:4][C:3]=1[C:12]([C:14]1[CH:15]=[CH:16][C:17]([CH:20]2[CH2:21][CH2:22]2)=[CH:18][CH:19]=1)=[O:13])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 59259036HCID 59259036, compound

Product 1

HCID 59259056HCID 59259056, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 490 mg (1.68 mmol) of the aniline prepared in step D, 256 μl benzaldehyde and 150 μl AcOH in 5 ml MeOH is treated with 200 mg 95% sodium cyanoborohydride. Temperature is kept around rt by a cooling bath. After 5 hours the reaction mixture is distributed between water and ethyl acetate. The crude orange oil obtained after concentration i.V. is purified by chromatography (hexane/ethyl acetate) to yield a yellow solid. m.p. 116-118° C.

Workup

  1. customTemperature is kept around rt by a cooling bath
  2. customThe crude orange oil obtained
  3. concentrationafter concentration i.V
  4. customis purified by chromatography (hexane/ethyl acetate)
  5. customto yield a yellow solid

Sources & evidence

ORD record
ord-2bf16342c0c64f9fa337c3241b2fda68
Source dataset
uspto-grants-2010_04
Patent number
US07696216B2

Reaction notes

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