Sodium Hydroxide → HCID 22501979, compound

HRID 1947650Notes

Reaction equation

HRID 1947650 reaction equation
[BH4-].[Na+].[CH:3]([N:6]1[C:14](=[O:15])[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([N+:16]([O-])=O)[CH:12]=2)[C:7]1=[O:19])([CH3:5])[CH3:4].O.O.[Sn](Cl)Cl.[OH-].[Na+]>C(O)C>[NH2:16][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:19])[N:6]([CH:3]([CH3:4])[CH3:5])[C:14]2=[O:15]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 61436Stannous chloride dihydrateHCID 4017380HCID 4017380, compoundHCID 4311764Sodium borohydride

Product 1

HCID 22501979HCID 22501979, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of sodium borohydride (193 mg, 5.12 mmol) in ethanol (4 ml) was added dropwise to a stirred solution of 2-isopropyl-5-nitro-isoindole-1,3-dione (1.20 g, 5.12 mmol) and tin (II) dichloride dihydrate (3.47 g, 15.36 mmol) in ethanol (40 ml) at 60° C. The resulting solution was stirred for 2 hrs, after which time the reaction was cooled to 0° C. and basified using 2M sodium hydroxide. The aqueous phase was extracted with dichloromethane (3×20 ml) and the combined organics washed with brine, then dried (MgSO4) and evaporated in vacuo. The crude residue was purified by preparative HPLC (Method D) to afford the title compound as a yellow solid (512 mg, 49%). HPLC retention time 7.2 min. Mass spectrum (ES+) m/z 205 (M+H).

Workup

  1. extractionThe aqueous phase was extracted with dichloromethane (3×20 ml)
  2. washthe combined organics washed with brine
  3. dry with materialdried (MgSO4)
  4. customevaporated in vacuo
  5. customThe crude residue was purified by preparative HPLC (Method D)

Sources & evidence

ORD record
ord-22b20f59d0ac455b80916a90a4996a11
Source dataset
uspto-grants-2013_03
Patent number
US08399481B2

Reaction notes

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