Acetic Acid → HCID 18626090, compound

HRID 1859673Notes

Reaction equation

HRID 1859673 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[CH:6]=O.[NH2:13][C:14]1[CH:15]=[C:16]([CH:26]=[CH:27][C:28]=1[O:29][CH3:30])[C:17]([NH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:18].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[CH2:6][NH:13][C:14]1[CH:15]=[C:16]([CH:26]=[CH:27][C:28]=1[O:29][CH3:30])[C:17]([NH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:18]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 8419VeratraldehydeHCID 84263-Amino-4-methoxybenzanilideHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 18626090HCID 18626090, compoundYield 63.7%

Procedure

Prepared according to the procedure of Example 50 using 3,4-dimethoxybenzaldehyde (1.94 g, 11.6 mmol), 3-amino-4-methoxy-N-phenyl-benzamide (2.8 g, 11.6 mmol), acetic acid (0.69 g, 11.5 mmol), and sodium triacetoxyborohydride (2.6 g, 11.7 mmol) to afford the product (2.9 g); m.p. 187-188° C. after recrystallization from ethanol.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-0432b81d4b7c4bba9d1615c8b92c0318
Source dataset
uspto-grants-2003_03
Patent number
US06528528B2

Reaction notes

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