Dimethylacetamide → HCID 59549438, compound

HRID 1947774Notes

Reaction equation

HRID 1947774 reaction equation
[NH2:1][C:2]1[C:10](Br)=[C:9]2[C:5]([CH2:6][CH2:7][CH:8]2[OH:12])=[CH:4][CH:3]=1.C[C:14]([N:16](C)C)=O>[C-]#N.[Zn+2].[C-]#N.[Zn].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2]>[NH2:1][C:2]1[C:10]([C:14]#[N:16])=[C:9]2[C:5]([CH2:6][CH2:7][CH:8]2[OH:12])=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 31374DimethylacetamideHCID 685011896-Amino-7-bromoindan-1-ol

Product 1

HCID 59549438HCID 59549438, compound

Reagents, catalysts & solvents 3

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 23994ZincCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)Catalyst

Conditions

Temperature
140 °C

Procedure

A suspension of 6-amino-7-bromoindan-1-ol (1 g, 4.3 mmol), zinc cyanide (290 mg, 2.6 mmol), zinc (140 mg, 2.1 mmol), Pd(dba)3 (10 mol %), and dppf (50 mol %) in dimethylacetamide (8 ml) is heated at 140° C. under nitrogen for six hours. The solvent is distilled off at 100° C. under vacuum, the residue treated with dichloromethane, filtered through Celite, and the filtrate is washed with water. The organic layer is separated, dried over sodium sulfate, filtered, and evaporated. Chromatographic purification by using ethyl acetate/hexane as eluent gives 6-amino-7-cyanoindan-1-ol as solid; LC/MS: 175 (M+1)+.

Workup

  1. distillationThe solvent is distilled off at 100° C. under vacuum
  2. additionthe residue treated with dichloromethane
  3. filtrationfiltered through Celite
  4. washthe filtrate is washed with water
  5. customThe organic layer is separated
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customChromatographic purification

Sources & evidence

ORD record
ord-d874f7d45d1648088b03b62111abbfe4
Source dataset
uspto-grants-2013_03
Patent number
US08399490B2

Reaction notes

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