Ammonium Chloride → Ethyl 7-(2-amino-4-carbamoylphenoxy)-6-chlorochroman-4-carboxylate

HRID 1626409Notes

Reaction equation

HRID 1626409 reaction equation
[C:1]([C:4]1[CH:26]=[CH:25][C:7]([O:8][C:9]2[CH:18]=[C:17]3[C:12]([CH:13]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:14][CH2:15][O:16]3)=[CH:11][C:10]=2[Cl:24])=[C:6]([N+:27]([O-])=O)[CH:5]=1)(=[O:3])[NH2:2].[Cl-].[NH4+]>C1COCC1.[Zn]>[NH2:27][C:6]1[CH:5]=[C:4]([C:1](=[O:3])[NH2:2])[CH:26]=[CH:25][C:7]=1[O:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:14][CH2:15][O:16]2)=[CH:11][C:10]=1[Cl:24]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 67287592Ethyl 7-(4-carbamoyl-2-nitrophenoxy)-6-chlorochroman-4-carboxylate

Product 1

HCID 67288481Ethyl 7-(2-amino-4-carbamoylphenoxy)-6-chlorochroman-4-carboxylateYield 83%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of ethyl 7-(4-carbamoyl-2-nitrophenoxy)-6-chlorochroman-4-carboxylate (7.74 g, 18.4 mmol) in THF (130 mL) at ambient temperature was added zinc dust followed by saturated ammonium chloride solution (50 mL). The resulting mixture was stirred at ambient temperature. After 30 minutes the reaction was filtered through a glass microfibre filter and the insoluble material was washed twice with THF. The combined filtrate and washings were concentrated and the residue was diluted with ethyl acetate (250 mL) and water (125 mL). The organic layer was separated and washed with brine (75 mL), dried over sodium sulfate and evaporated to provide the desired product (5.95 g, 83%).

Workup

  1. filtrationAfter 30 minutes the reaction was filtered through a glass microfibre
  2. filtrationfilter
  3. washthe insoluble material was washed twice with THF
  4. concentrationThe combined filtrate and washings were concentrated
  5. additionthe residue was diluted with ethyl acetate (250 mL) and water (125 mL)
  6. customThe organic layer was separated
  7. washwashed with brine (75 mL)
  8. dry with materialdried over sodium sulfate
  9. customevaporated

Sources & evidence

ORD record
ord-3ae3669ffc06456aa25bf78664cd5ac4
Source dataset
uspto-grants-2014_07
Patent number
US08785445B2

Reaction notes

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