Formic Acid → HCID 86691456, compound

HRID 1618858Notes

Reaction equation

HRID 1618858 reaction equation
[C:1]([C:3]([C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH3:30])[CH:24]=1)([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:4][CH:5]([N:7]([CH3:16])C(=O)OCC(Cl)(Cl)Cl)[CH3:6])#[N:2].C(O)=O>O1CCCC1.[Zn]>[CH3:30][O:29][C:25]1[CH:24]=[C:23]([C:3]2([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:4][CH:5]([CH3:6])[N:7]([CH3:16])[C:1]2=[NH:2])[CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 2

HCID 284Formic AcidHCID 86691454HCID 86691454, compound

Product 1

HCID 86691456HCID 86691456, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

The product of Step 3 (40 g) was dissolved in tetrahydrofuran (500 mL). The solution was cooled to 0° C. using ice bath and stirred under Argon for 30 min. Then, 60 g zinc dust followed by 60 mL of formic acid (90%) was added to the reaction mixtures and stirring continued at 0° C. for 3 hr under argon purging. The stifling was continued at 25° C. for 16 hr under argon purging. Then, the reaction mixture was filtered and concentrated under vacuum. Crude Step 4 product was carried forward without purification.

Workup

  1. additionwas added to the reaction mixtures
  2. stirringstirring
  3. waitcontinued at 0° C. for 3 hr under argon purging
  4. waitThe stifling was continued at 25° C. for 16 hr under argon purging
  5. filtrationThen, the reaction mixture was filtered
  6. concentrationconcentrated under vacuum
  7. customCrude Step 4 product was carried forward without purification

Sources & evidence

ORD record
ord-624387928de04a96a080370701fad346
Source dataset
uspto-grants-2014_07
Patent number
US08771964B2

Reaction notes

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