HCID 66665338, compound → HCID 58056159, compound

HRID 1773550Notes

Reaction equation

HRID 1773550 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([C:12](O)=[O:13])=[CH:9]2)=[CH:4][C:3]=1[O:15][CH3:16]>O1CCCC1>[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH2:12][OH:13])=[CH:9]2)=[CH:4][C:3]=1[O:15][CH3:16]

Participants

3

Reactant 1

HCID 66665338HCID 66665338, compound

Product 1

HCID 58056159HCID 58056159, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Borane tetrahydrofuran complex (1 mL, 0.92 mmol) was added, at 0° C., to a suspension of 7-amino-6-methoxy-naphthalene-2-carboxylic acid (0.1 g, 0.46 mmol) in anhydrous tetrahydrofuran (2 mL) and the resulting mixture was stirred at room temperature overnight. The reaction mixture was quenched by addition of methanol and then was stirred for 2 hours at room temperature. The resulting mixture was concentrated under reduced pressure, partitioned between dichloromethane and a saturated aqueous solution of sodium bicarbonate. The organic layer was separated, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to afford (7-amino-6-methoxy-naphthalen-2-yl)-methanol without further purifications. MS=204 [M+H]+.

Workup

  1. customThe reaction mixture was quenched by addition of methanol
  2. stirringwas stirred for 2 hours at room temperature
  3. concentrationThe resulting mixture was concentrated under reduced pressure
  4. custompartitioned between dichloromethane
  5. customThe organic layer was separated
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-5df4dff09f2a48cabc4514671ef0b93f
Source dataset
uspto-grants-2016_02
Patent number
US09255110B2

Reaction notes

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