Hydrochloric Acid → HCID 51063817, compound

HRID 383323Notes

Reaction equation

HRID 383323 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:10][CH2:9][CH:8]([C:11]([O:13]CC)=[O:12])[O:7][C:6]=2[CH:16]=1.[OH-].[Na+].Cl>O>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:10][CH2:9][CH:8]([C:11]([OH:13])=[O:12])[O:7][C:6]=2[CH:16]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 18788323Ethyl 7-methyl-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylate

Product 1

HCID 51063817HCID 51063817, compoundYield 68.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To the suspension of ethyl 7-methyl-3,4-dihydro-2H-benzo[b][1,4]oxazine-2-carboxylate (8.5 g, 38.5 mmol) in water (60 mL) was added NaOH (3.8 g, 96.1 mmol). The suspension was stirred at 100° C. for 30 min under N2 atmosphere. The reaction was cooled to room temperature and acidified to pH 2 with conc. HCl. The resulting precipitate was filtered, washed with water and dried to obtain 7-methyl-3,4-dihydro-2H-benzo[b][1,4]oxazine-2-carboxylic acid (5.1 g, 68.7%). 1H NMR (400 MHz, DMSO-d6) δ 6.51 (s, 1H), 6.46-6.41 (m, 2H), 5.60 (br s, 1H), 4.73 (t, J=3.6 Hz, 1H), 3.33-3.31 (m, 2H), 2.10 (s, 3H).

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. filtrationThe resulting precipitate was filtered
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-f57b9ff9cab442fe88d2d2ffa03f7318
Source dataset
uspto-grants-2013_02
Patent number
US08367660B2

Reaction notes

Loading…