Sodium Hydroxide → HCID 57681687, compound

HRID 1865158Notes

Reaction equation

HRID 1865158 reaction equation
[BH4-].[Na+].[OH-].[Na+].[H][H].[NH2:7][C:8]1[CH:9]=[C:10]2[C:19](=[CH:20][CH:21]=1)[N:18]=[C:17]1[C:12](=[CH:13][C:14](=[O:28])[C:15](Cl)=[C:16]1CCCCC)[O:11]2.NC1C=C2C(=CC=1)N=C1C(=CC(=O)C=C1CCCCC)O2>O.CN(C)C=O.O1CCCC1.[Pd].C(O)(=O)C>[CH:21]1[C:8]([NH2:7])=[CH:9][C:10]2[O:11][C:12]3[C:17](=[N:18][C:19]=2[CH:20]=1)[CH:16]=[CH:15][C:14](=[O:28])[CH:13]=3

Participants

11

Reactant 5

HCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 67103145HCID 67103145, compoundHCID 67103409HCID 67103409, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57681687HCID 57681687, compound

Reagents, catalysts & solvents 5

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

Acetic acid (30%, 200 cm3) from a 2-necked flask was added, dropwise, while stirring, to a solution consisting of approximately 5 g of sodium borohydride and 200 mg of sodium hydroxide dissolved in 200 cm3 of water. Hydrogen gas was passed through a 3-necked flask in which the mixture of 7-amino-2-chloro-1-pentylphenoxazin-3-one and 7-amino-1-pentylphenoxazin-3-one (0.564 g) was dissolved in anhydrous dimethylformamide (15 cm3 by heating and then cooling) and the solution was diluted with anhydrous tetrahydrofuran (THF) (15 cm3). A Pd/C catalyst (5%, 200 mg) was added to the solution. The solution was sparged gently with hydrogen gas and this was continued for a long time after the apparent reduction (approximately 1 h). The reduction was demonstrated by the solution turning from a purple color to a grayish-green color. A solution of resorufamine was thus obtained.

Workup

  1. temperatureby heating
  2. temperaturecooling) and the solution
  3. customThe solution was sparged gently with hydrogen gas
  4. customafter the apparent reduction (approximately 1 h)

Sources & evidence

ORD record
ord-68e67c5841874a788dff8e8e7c9bfaa6
Source dataset
uspto-grants-2009_12
Patent number
US07626018B2

Reaction notes

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