Acetic Acid → HCID 69659346, compound

HRID 1829019Notes

Reaction equation

N[C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][O:7][C:8]2=[C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[NH:13][C:12]2=[O:20])=[CH:4][CH:3]=1.[CH2:21]=O.[C:23]([BH3-])#[N:24].[Na+].C[C:28](O)=[O:29]>>[CH3:21][N:24]([CH3:23])[C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][O:7][C:8]2=[C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]([CH2:28][OH:29])[C:12]2=[O:20])=[CH:4][CH:3]=1

Participants

Reactant 4

HCID 176Acetic Acid

HCID 712Formaldehyde

HCID 5003444Sodium cyanoborohydride

HCID 696591993-(6-Amino-2-benzofuran-1(3H)-ylidene)-1,3-dihydro-2H-indol-2-one

Product 1

HCID 69659346HCID 69659346, compound

Procedure

To a suspension of 3-(6-amino-3H-isobenzofuran-1-ylidene)-1,3-dihydro-indol-2-one (100 mg, 0.378 mmole) were added saturated formaldehyde aqueous solution, and sodium cyanoborohydride (300 mg, 4.77 mmole). The resulting mixture was stirred at room temperature for 1 hour, and then was acidified with 10% AcOH aqueous solution. After stirred for another 10 minutes, the reaction was partitioned between CHCl3 and saturated NaHCO3 aqueous solution. The aqueous layer was extracted with CHCl3 (2×5 ml). The combined organic layers were washed with brine, and then dried over anhydrous MgSO4. Removal of the solvent afforded a crude product. Recrystallization of the crude product from MeOH led to 3-(6-dimethylamino-3H-isobenzofuran-1-ylidene)-1-hydroxymethyl-1,3-dihydro-indol-2-one as a yellow solid (90 mg, 74%).

Workup

stirringAfter stirred for another 10 minutes
customthe reaction was partitioned between CHCl3 and saturated NaHCO3 aqueous solution
extractionThe aqueous layer was extracted with CHCl3 (2×5 ml)
washThe combined organic layers were washed with brine
dry with materialdried over anhydrous MgSO4
customRemoval of the solvent

Sources & evidence

ORD record: ord-518c7dee1a2d479195a3e0966e1998a6
Source dataset: uspto-grants-2006_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07060844B2

Reaction notes

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