Hydrochloric Acid → HCID 69204693, compound

HRID 898301Notes

Reaction equation

HRID 898301 reaction equation
Cl[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[O:10]1[C:14]2[CH:15]=[CH:16][C:17]([CH2:19][C:20]#[N:21])=[CH:18][C:13]=2[O:12][CH2:11]1.CC(C)([O-])C.[K+].Cl[CH2:29][C:30]([O:32][CH3:33])=[O:31].Cl>CN(C)C=O.C1(C)C=CC=CC=1.CCCCCCC>[CH3:33][O:32][C:30]([C:29]1[C:19]([C:17]2[CH:16]=[CH:15][C:14]3[O:10][CH2:11][O:12][C:13]=3[CH:18]=2)([C:20]#[N:21])[C:2]2[C:3]([C:4]=1[NH2:5])=[CH:6][CH:7]=[CH:8][CH:9]=2)=[O:31]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 7295Methyl chloroacetateHCID 133912-ChlorobenzonitrileHCID 781783,4-(Methylenedioxy)phenylacetonitrileHCID 23665647Potassium tert-butoxide

Product 1

HCID 69204693HCID 69204693, compoundYield 79%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent2×HCID 8900HeptaneSolvent

Procedure

A mixture of 2-chlorobenzonitrile (12.3 g) and benzo[1,3]dioxol-5-yl-acetonitrile (10 g) in dimethylformamide (25 mL) was added with stirring and cooling in an ice bath to potassium tert-butoxide (20.1 g) dissolved in dimethylformamide (50 mL) at such a rate that the temperature did not exceed 25° C. After stirring for 0.5 h, methyl chloroacetate (11.1 g) was added in 10 min. After being stirred for 24 h at rt, the mixture was poured into a mixture of 0.1 M HCl (200 mL), heptane (30 mL) and toluene (15 mL). Stirring for 1 h, filtration and washing with water (2×50 mL), toluene (2×10 mL) and heptane (2×25 mL) afforded 79% of 3-Amino-1-benzo[1,3]dioxol-5-yl-1-cyano-1H-indene-2-carboxylic acid methyl ester.

Workup

  1. additionwas added
  2. customdid not exceed 25° C
  3. stirringAfter stirring for 0.5 h
  4. stirringAfter being stirred for 24 h at rt
  5. stirringStirring for 1 h
  6. filtrationfiltration
  7. washwashing with water (2×50 mL), toluene (2×10 mL) and heptane (2×25 mL)

Sources & evidence

ORD record
ord-e7bc07fcab3e4cc9a03e900dacfd1f8d
Source dataset
uspto-grants-2008_04
Patent number
US07351734B2

Reaction notes

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