Ammonium Chloride → HCID 90037473, compound

HRID 1055398Notes

Reaction equation

HRID 1055398 reaction equation
[NH2:1][CH:2]1[C:8]2([CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[O:7][C:6]2[C:14](F)=[C:15]([F:18])[CH:16]=[CH:17][C:5]=2[NH:4][C:3]1=[O:20].[NH4+].[Cl-].FC1C=C(F)C=CC=1[N+]([O-])=O>[Zn]>[NH2:1][CH:2]1[C:8]2([CH2:9][CH2:10][O:11][CH2:12][CH2:13]2)[O:7][C:6]2[CH:14]=[C:15]([F:18])[CH:16]=[CH:17][C:5]=2[NH:4][C:3]1=[O:20]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 679672,4-DifluoronitrobenzeneHCID 90037993HCID 90037993, compound

Product 1

HCID 90037473HCID 90037473, compound

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Procedure

In a similar manner to that described for the preparation of 3-amino-8,9-difluoro-2′,3′,5′,6′-tetrahydro-3H-spiro[benzo[b][1,4]oxazepine-2,4′-pyran]-4(5H)-one except in step 2 2.5 eq. of NH4Cl and 12 eq. of Zn were used, in step 3 the mixture was stirred for 6 h and in step 4 the mixture was hydrogenated overnight, 2,4-difluoronitrobenzene (2.69 g, 1.79 mL, 16.9 mmol) was converted to the title compound as a beige solid (110 mg) which was used without purification.

Workup

  1. waitwas hydrogenated overnight

Sources & evidence

ORD record
ord-424e04212bb0493cac315fa8d7955358
Source dataset
uspto-grants-2016_07
Patent number
US09394263B2

Reaction notes

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