Ethyl Acetate → HCID 9864638, compound

HRID 990930Notes

Reaction equation

[NH2:1][C:2]1[CH:18]=[CH:17][C:5]2[N:6]([CH2:12][C:13]([F:16])([F:15])[F:14])[CH2:7][CH:8]([CH2:10][CH3:11])[O:9][C:4]=2[CH:3]=1.CCO[C:22]([CH3:24])=[O:23]>>[CH2:10]([CH:8]1[O:9][C:4]2[C:5](=[CH:17][C:18]3[C:12]([C:13]([F:16])([F:15])[F:14])=[CH:24][C:22](=[O:23])[NH:1][C:2]=3[CH:3]=2)[N:6]([CH2:12][C:13]([F:16])([F:15])[F:14])[CH2:7]1)[CH3:11]

Participants

Reactant 2

HCID 8857Ethyl Acetate

HCID 16659359HCID 16659359, compound

Product 1

HCID 9864638HCID 9864638, compound

Procedure

(±)-7-Amino-2-ethyl-3,4-dihydro-4-(2,2,2-trifluoroethyl)-2H-1,4-benzoxazine (Structure 5 of Scheme I, where R6=Et, Rx=CF3). This compound was prepared by General Method 4 (EXAMPLE 1) from (±)-2-ethyl-3,4-dihydro-7-nitro-4-(2,2,2-trifluoroethyl)-2H-1,4-benzoxazine (170 mg, 0.6 mmol) and purified by flash chromatography (CH2Cl2/MeOH, 20:1) to afford 151 mg (99%) of (±)-7-amino-2-ethyl-3,4-dihydro-4-(2,2,2-trifluoroethyl)-2H-1,4-benzoxazine. Data for (±)-7-amino-2-ethyl-3,4-dihydro-4-(2,2,2-trifluoroethyl)-2H-1,4-benzoxazine: Rf 0.62 (3:2 EtOAc:hexanes); 1H NMR (400 MHz, CDCl3) δ 6.56 (d, 1H, J=8.0), 6.25-6.20 (m, 2H), 3.93 (m, 1H), 3.70-3.64 (m, 3H), 3.43 (br s, 1H), 3.31 (m, 1H), 3.12 (dd, 1H, J=11.9, 8.1), 1.74-1.59 (m, 2H), 1.04 (t, 3H, J=7.5).

Sources & evidence

ORD record: ord-fd2bbd8ce0dd4c0db20fa6ca175a49a0
Source dataset: uspto-grants-2002_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06462038B1

Reaction notes

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