Water → HCID 67040481, compound

HRID 605095Notes

Reaction equation

HRID 605095 reaction equation
[CH2:1]([O:8][C:9]1[CH:27]=[CH:26][C:12]([O:13][C:14]2[CH:22]=[CH:21][C:17]([C:18]([OH:20])=[O:19])=[CH:16][C:15]=2[N+:23]([O-])=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[NH4+].O>CO.O1CCCC1.[Fe]>[NH2:23][C:15]1[CH:16]=[C:17]([CH:21]=[CH:22][C:14]=1[O:13][C:12]1[CH:26]=[CH:27][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:10][CH:11]=1)[C:18]([OH:20])=[O:19]

Participants

7

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 67040724HCID 67040724, compound

Product 1

HCID 67040481HCID 67040481, compoundYield 100%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 887MethanolSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of the product of Example 43A (0.73 g, 2.0 mmol), iron powder (1.12 g, 20 mmol) and ammonium chloride (1.08 g, 20 mmol) in methanol (20 mL), tetrahydrofuran (20 mL), and water (10 mL) was heated at 80° for 48 hours. After cooling to room temperature, the mixture was diluted with methanol (50 mL) and filtered through a pad of celite. The filtrate was concentrated under vacuum then purified by column chromatography on silica gel using methanol/dichloromethane as eluent to provide the title product (670 mg, 100%).

Workup

  1. filtrationfiltered through a pad of celite
  2. concentrationThe filtrate was concentrated under vacuum
  3. customthen purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-018338e60b5e4970a3ff3eebd603366d
Source dataset
uspto-grants-2011_03
Patent number
US07910595B2

Reaction notes

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