HCID 90409179, compound → 2H-1,4-Benzoxazin-5-amine, 3,4-dihydro-3-phenyl-

HRID 589018Notes

Reaction equation

HRID 589018 reaction equation
[N+:1]([C:4]1[C:9]2[N:10]=[C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:12][O:13][C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-])=O>CO>[C:14]1([CH:11]2[NH:10][C:9]3=[C:4]([NH2:1])[CH:5]=[CH:6][CH:7]=[C:8]3[O:13][CH2:12]2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

3

Reactant 1

HCID 90409179HCID 90409179, compound

Product 1

HCID 904094562H-1,4-Benzoxazin-5-amine, 3,4-dihydro-3-phenyl-

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The 5-nitro-3-phenyl-2H-1,4-benzoxazine oil was taken up in MeOH (50 mL) in a Parr shaker bottle, deoxygenated with nitrogen, the catalyst 10% Pd on carbon (0.25 g) was added, the reaction vessel was charged to 55 psi with hydrogen and shaken. After 2 h the reaction was complete by LC/MS. The reaction was filtered to remove the catalyst and concentrated under reduced pressure to give 3-phenyl-3,4-dihydro-2H-1,4-benzoxazin-5-amine as a dark oil. (3.5 g, 97%). LCMS calc. for C14H15N2O (M+H)+: m/z=227.1. found: 227.1. 1H NMR (500 MHz, DMSO-d6) δ 7.44 (d, J=7.4 Hz, 2H), 7.37 (dd, J=7.5 Hz, 2H), 7.31 (t, J=7.2 Hz, 1H), 6.35 (dd, J=7.9 Hz, 1H), 6.21 (dd, J=7.8, 1.0 Hz, 1H), 6.07 (d, J=7.9 Hz, 1H), 5.00 (s, 1H), 4.62 (s, 2H), 4.44 (dd, J=4.9, 2.6 Hz, 1H), 4.21-4.13 (m, 1H), 3.87 (dd, J=10.4, 7.7 Hz, 1H).

Workup

  1. customdeoxygenated with nitrogen
  2. additionthe catalyst 10% Pd on carbon (0.25 g) was added
  3. additionthe reaction vessel was charged to 55 psi with hydrogen
  4. filtrationThe reaction was filtered
  5. customto remove the catalyst
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c698d6f284c3467aa69f95b5809b94e8
Source dataset
uspto-grants-2016_01
Patent number
US09227985B2

Reaction notes

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