7-Nitro-4-(2-(pyrrolidin-1-yl)ethyl)-2H-benzo[b][1,4]oxazin-3(4H)-one → 7-Amino-4-(2-(pyrrolidin-1-yl)ethyl)-2H-benzo[b][1,4]oxazin-3(4H)-one

HRID 424466Notes

Reaction equation

HRID 424466 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[N:12]([CH2:13][CH2:14][N:15]3[CH2:19][CH2:18][CH2:17][CH2:16]3)[C:11](=[O:20])[CH2:10][O:9][C:8]=2[CH:21]=1)([O-])=O>C(O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]2[N:12]([CH2:13][CH2:14][N:15]3[CH2:16][CH2:17][CH2:18][CH2:19]3)[C:11](=[O:20])[CH2:10][O:9][C:8]=2[CH:21]=1

Participants

4

Reactant 1

HCID 591441157-Nitro-4-(2-(pyrrolidin-1-yl)ethyl)-2H-benzo[b][1,4]oxazin-3(4H)-one

Product 1

HCID 591441107-Amino-4-(2-(pyrrolidin-1-yl)ethyl)-2H-benzo[b][1,4]oxazin-3(4H)-oneYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 7-nitro-4-(2-(pyrrolidin-1-yl)ethyl)-2H-benzo[b][1,4]oxazin-3(4H)-one (0.46 g, 1.579 mmol) in dry ethanol (5 mL) was treated with Pd—C (˜0.05 g) and purged with hydrogen gas. The reaction was stirred under hydrogen atmosphere (balloon pressure) for 4 hours. The reaction was filtered through a Celite bed and washed with methanol (3×10 mL). The combined organic layers were evaporated and dried under vacuum to obtain the crude title compound (0.4 g, 97%) as a solid. 1H NMR (DMSO-d6) δ 1.61-1.70 (m, 4H), 2.44-2.56 (m, 6H, merged with DMSO-d6), 3.90 (t, 2H, J=7.2 Hz), 4.47 (s, 2H), 5.01 (s, 2H), 6.22 (d, 1H, J=2.4 Hz), 6.25 (dd, 1H, J=2.4, 8.2 Hz), 6.84 (d, 1H, J=8.7 Hz); ESI-MS (m/z, %): 262 (MH+, 100), 191 (44).

Workup

  1. custompurged with hydrogen gas
  2. filtrationThe reaction was filtered through a Celite bed
  3. washwashed with methanol (3×10 mL)
  4. customThe combined organic layers were evaporated
  5. customdried under vacuum

Sources & evidence

ORD record
ord-0e20c3116c0a4b73bc74d583a2e96698
Source dataset
uspto-grants-2012_01
Patent number
US08106043B2

Reaction notes

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