Ammonium Chloride → HCID 70662764, compound

HRID 2370059Notes

Reaction equation

HRID 2370059 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]=[C:9]2[NH:14][C:13](=[O:15])[C:12](=[CH:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20]C=3)[NH:11][C:10]2=[O:24])=[N:6][CH:7]=1.[NH4+].[Cl-]>CN(C=O)C.[Zn]>[CH2:16]([CH:12]1[NH:11][C:10](=[O:24])/[C:9](=[CH:8]/[C:5]2[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][N:6]=2)/[NH:14][C:13]1=[O:15])[C:17]1[CH:18]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 69132345HCID 69132345, compound

Product 1

HCID 70662764HCID 70662764, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 6228DimethylformamideSolvent

Procedure

Compound C in Example 1 was added to a solution of NH4Cl (10 eq, 0.3 M) in DMF with zinc powder (10 eq). The reaction was stirred in an ice bath for 2 hr. After the reaction was complete, the reaction mixture was filtered. The filtrate was collected and water (2× to DMF) was added. The solid precipitate was collected. The collected solids were combined, washed with water, and dried to give a white powder (yield: 78%). mp. 251-252° C. 1H-NMR (400 MHz, DMSO-d6) δ 3.04 (dd, J=4.0, 11.2 Hz, 1H), 3.13 (dd, J=3.6, 11.2 Hz, 1H), 4.32 (dd, J=4.0, 6.0 Hz, 1H), 6.41 (s, 1H), 7.01 (d, J=1.2 Hz, 2H, ArH), 7.24-7.36 (m, 5H, ArH), 7.92 (s, 1H, ArH), 8.26 (d, J=1.6 Hz, 1H, NH), 9.60 (s, 1H, OH), 9.71 (s, 1H, NH)

Workup

  1. filtrationthe reaction mixture was filtered
  2. customThe filtrate was collected
  3. additionwater (2× to DMF) was added
  4. customThe solid precipitate was collected
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-f3417eed5bd5476c8c1d36554f9ed863
Source dataset
uspto-grants-2014_04
Patent number
US08710062B2

Reaction notes

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