Ammonium Chloride → Ethyl 2-amino-5-(benzyloxy)-4-fluorobenzoate

HRID 1022482Notes

Reaction equation

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

Participants

Conditions

Temperature: 90 °C

Procedure

1.76 g of NH4Cl dissolved in 21 ml of water are added to a mixture heated to 90° C. of 7.0 g of the compound obtained in Step 4.1, and 4.44 g of Fe(0) in 400 ml of isopropanol and 100 ml of THF. The reaction mixture is heated for 4 hours at 90° C. A further 0.88 g of NH4Cl is added and the mixture is heated for 2 hours at 90° C. The resulting mixture is filtered while hot and the filtrate is evaporated under reduced pressure. The residue is taken up in EtOAc and washed twice with saturated NaHCO3 solution. The organic phase is dried over MgSO4 and filtered, and the filtrate is evaporated under reduced pressure. The residue is chromatographed on silica gel, eluting with a PE/EtOAc mixture from (100/0, v/v) to (40/60, v/v) to give 5.2 g of the expected product.

Workup

additionare added to a mixture
temperaturethe mixture is heated for 2 hours at 90° C
filtrationThe resulting mixture is filtered while hot and the filtrate
customis evaporated under reduced pressure
washwashed twice with saturated NaHCO3 solution
dry with materialThe organic phase is dried over MgSO4
filtrationfiltered
customthe filtrate is evaporated under reduced pressure
customThe residue is chromatographed on silica gel
washeluting with a PE/EtOAc mixture from (100/0

Sources & evidence

ORD record: ord-9376898b46c241288c347f0fe15abec6
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722659B2

Reaction notes

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