Sodium Bicarbonate → HCID 23365858, compound

HRID 1646341Notes

Reaction equation

HRID 1646341 reaction equation
[CH3:1][C:2]([CH3:30])=[CH:3][CH2:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([N+:14]([O-])=O)=[CH:11][CH:12]=2)[C:7]([CH2:17][C:18]2[CH:27]=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][C:19]=2[O:28][CH3:29])=[CH:6]1.C(=O)(O)[O-].[Na+]>C(O)C>[NH2:14][C:10]1[CH:9]=[C:8]2[C:13](=[CH:12][CH:11]=1)[N:5]([CH2:4][CH:3]=[C:2]([CH3:30])[CH3:1])[CH:6]=[C:7]2[CH2:17][C:18]1[CH:27]=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][C:19]=1[O:28][CH3:29]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 23365895HCID 23365895, compound

Product 1

HCID 23365858HCID 23365858, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A slurry of methyl 4-[1-(3-methylbut-2-enyl)-5-nitroindol-3-ylmethyl]-3-methoxybenzoate (0.22 g.) and stannous chloride dihydrate (1.6 g.) in absolute ethanol (8 ml.) was heated and stirred under reflux under an atmosphere of nitrogen for 24 hours. The cooled mixture was poured into saturated sodium bicarbonate solution (30 ml.). The mixture obtained was extracted with dichloromethane (2×30 ml.). The combined extracts were washed with saturated brine (25 ml.), dried and evaporated to give methyl 4-[5-amino-1-(3-methylbut-2-enyl)indol-3-ylmethyl]-3-methoxybenzoate (F) (0.14 g.: 69%) an oil; NMR: 1.68 (s,3 H, =C--CH3), 1.76 (s,3 H, =C--CH3), 3.82 (s,3 H, CO.OCH3), 3.89 (s,2 H, CH2.Ar), 3.91 (s,3 H, OCH3), 4.57 (d,2 H, CH2N), 5.27 (t,1 H, CH2CH), 6.48 (m,2 H), 6.91 (s,1 H), 7.04 (d,1 H), 7.08 (d,1 H), 7.46 (m,2 H).

Workup

  1. temperatureunder reflux under an atmosphere of nitrogen for 24 hours
  2. customThe mixture obtained
  3. extractionwas extracted with dichloromethane (2×30 ml.)
  4. washThe combined extracts were washed with saturated brine (25 ml.)
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-5d35980b9ea74b46a86fcac123ee8e3c
Source dataset
uspto-grants-1993_01
Patent number
US05179112

Reaction notes

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