Hydrochloric Acid → HCID 58056952, compound

HRID 1480744Notes

Reaction equation

HRID 1480744 reaction equation
[H-].[Na+].[C:3]([CH2:5][C:6]([NH2:8])=[O:7])#[N:4].F[C:10]1[CH:19]=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][C:11]=1[N+:20]([O-:22])=[O:21].Cl>CN(C=O)C.O>[NH2:8][C:6](=[O:7])[CH:5]([C:10]1[CH:19]=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][C:11]=1[N+:20]([O-:22])=[O:21])[C:3]#[N:4]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7898CyanoacetamideHCID 24758Sodium hydrideHCID 5219721Methyl 4-fluoro-3-nitrobenzoate

Product 1

HCID 58056952HCID 58056952, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

NaH (3.41 g, 85 mmol) was added portionwise to a cold solution of 2-cyanoacetamide (7.18 g, 85 mmol) in DMF (53 mL). After 30 minutes at room temperature, a solution of methyl 4-fluoro-3-nitrobenzoate (8.5 g, 42.7 mmol) in 15 mL of DMF was added dropwise. After 3 hours a mixture of ice, water and 12 mL HCl (10%) were added. The resulting solid was filtered, rinsed with water and dried under high vacuum overnight to give 9.1 g of methyl 4-(2-amino-1-cyano-2-oxoethyl)-3-nitrobenzoate: 1H NMR (400 MHz, DMSO-d6) δ ppm 3.93 (s, 3H) 5.78 (s, 1H) 7.77 (s, 1H) 7.91 (d, J=7.83 Hz, 1H) 8.04 (s, 1H) 8.39 (dd, J=8.02, 1.76 Hz, 1H) 8.56 (d, J=1.56 Hz, 1H).

Workup

  1. additionwere added
  2. filtrationThe resulting solid was filtered
  3. washrinsed with water
  4. customdried under high vacuum overnight

Sources & evidence

ORD record
ord-68a8766a60264e62be7cf741d09c72f8
Source dataset
uspto-grants-2016_08
Patent number
US09409906B2

Reaction notes

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