Ethanol → HCID 67469341, compound

HRID 630420Notes

Reaction equation

HRID 630420 reaction equation
[NH2:1][C:2]1[C:11]([C:12]#[N:13])=[CH:10][C:5]([C:6](OC)=[O:7])=[C:4]([O:14][CH3:15])[CH:3]=1.[BH4-].[Li+].C(O)C.[Cl-].[NH4+]>O1CCCC1>[NH2:1][C:2]1[CH:3]=[C:4]([O:14][CH3:15])[C:5]([CH2:6][OH:7])=[CH:10][C:11]=1[C:12]#[N:13]

Participants

6

Reactant 4

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 4148881Lithium borohydrideHCID 67469370HCID 67469370, compound2×

Product 1

HCID 67469341HCID 67469341, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 4-amino-5-cyano-2-methoxybenzoate (intermediate 129; 0.59 g, 2.88 mmol) in tetrahydrofuran (40 mL) was added dropwise lithium tetrahydroborate 2M (21.7 mL, 43.4 mmol) at 0° C. under nitrogen atmosphere. After 5 minutes was added dropwise ethanol (7.5 mL). The mixture was stirred for five days at room temperature. Then the crude was poured into a saturated solution of ammonium chloride and ice, and stirred for 10 minutes. The crude was extracted with ethyl acetate and washed with water and brine, dried and the solvent was removed under reduced pressure to obtain the title compound as a white solid (81%).

Workup

  1. stirringstirred for 10 minutes
  2. extractionThe crude was extracted with ethyl acetate
  3. washwashed with water and brine
  4. customdried
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-c8ffdd81473c452e8f24b46e9006343c
Source dataset
uspto-grants-2016_04
Patent number
US09315463B2

Reaction notes

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